EP4376996A1 - Microcapsules à base de protéines végétales - Google Patents

Microcapsules à base de protéines végétales

Info

Publication number
EP4376996A1
EP4376996A1 EP22797327.8A EP22797327A EP4376996A1 EP 4376996 A1 EP4376996 A1 EP 4376996A1 EP 22797327 A EP22797327 A EP 22797327A EP 4376996 A1 EP4376996 A1 EP 4376996A1
Authority
EP
European Patent Office
Prior art keywords
protein
group
oil
perfume
shell
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP22797327.8A
Other languages
German (de)
English (en)
Inventor
Lahoussine Ouali
Anaick NICOLAE
Marlène JACQUEMOND
Laura ETCHENAUSIA
Valentina VALMACCO
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Firmenich SA
Original Assignee
Firmenich SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Firmenich SA filed Critical Firmenich SA
Publication of EP4376996A1 publication Critical patent/EP4376996A1/fr
Pending legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/06—Making microcapsules or microballoons by phase separation
    • B01J13/14—Polymerisation; cross-linking
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/20—After-treatment of capsule walls, e.g. hardening
    • B01J13/206—Hardening; drying
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0039—Coated compositions or coated components in the compositions, (micro)capsules
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C11D3/502—Protected perfumes
    • C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay

Definitions

  • the present invention relates to a new process for the preparation of plant protein-based microcapsules.
  • Plant protein-based microcapsules are also an object of the invention.
  • Perfuming compositions and consumer products comprising said microcapsules, in particular perfumed consumer products in the form of home care or personal care products, are also part of the invention.
  • Polyurea and polyurethane-based microcapsule slurry are widely used for example in perfumery industry for instance as they provide a long lasting pleasant olfactory effect after their applications on different substrates.
  • Those microcapsules have been widely disclosed in the prior art (see for example W02007/004166 or EP 2300146).
  • the present invention is proposing a solution to the above-mentioned problem by providing new plant protein-based microcapsules and a process for preparing said microcapsules. Summary of the invention
  • microcapsules of the invention therefore provide a solution to the above-mentioned problems as it allows preparing eco-friendly microcapsules with the desired stability in challenging bases.
  • the present invention relates to a core-shell microcapsule comprising: a core comprising a hydrophobic material, preferably a perfume oil, and a polymeric shell comprising a protein chosen in the group consisting of potato protein, chickpea protein, pea protein, algae protein, faba bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof.
  • Another object of the invention is a core-shell microcapsule slurry comprising at least one microcapsule, the microcapsule comprising: a core comprising a hydrophobic material, preferably a perfume oil, and a polymeric shell comprising a protein chosen in the group consisting of potato protein, chickpea protein, pea protein, algae protein, faba bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof.
  • Another object of the invention is a process for preparing a core-shell microcapsule slurry comprising the steps of: a) Preparing an oil phase comprising a hydrophobic material, preferably a perfume to form an oil phase; b) Dispersing the oil phase obtained in step a) into a water phase to form an oil-in water emulsion; c) Performing a curing step to form microcapsules in the form of a slurry; wherein a polyfunctional monomer is added in the oil phase and/or in the water phase, and wherein a protein chosen in the group consisting of potato protein, chickpea protein, pea protein, algae protein, faba bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof is added in the oil phase and/or in the water phase.
  • the present invention also relates to perfumed consumer products and flavoured edible products comprising the microcapsules defined above.
  • active ingredient it is meant a single compound or a combination of ingredients.
  • perfume or flavour oil it is meant a single perfuming or flavouring compound or a mixture of several perfuming or flavouring compounds.
  • consumer product or “end-product” it is meant a manufactured product ready to be distributed, sold and used by a consumer.
  • dispersion in the present invention it is meant a system in which particles are dispersed in a continuous phase of a different composition and it specifically includes a suspension or an emulsion.
  • a “microcapsule”, or the similar, in the present invention it is meant that core-shell microcapsules have a particle size distribution in the micron range (e.g. a mean diameter (d(v, 0.5)) comprised between about 1 and 3000 microns, preferably between 1 and 500 microns) and comprise an external solid polymeric shell and an internal continuous oil phase enclosed by the external shell.
  • the polymeric shell is a polyamide-based shell.
  • microcapsule slurry it is meant microcapsule(s) that is (are) dispersed in a liquid.
  • the slurry is an aqueous slurry, i.e the microcapsule(s) is (are) dispersed in an aqueous phase.
  • amino-compound it should be understood a compound having at least two reactive amine groups.
  • polyamide-based microcapsules By “polyamide-based microcapsules”, “polyamide-based core-shell microcapsules” or “polyamide-based shell”, it means that the microcapsule’s shell comprises a polyamide material.
  • the wording “polyamide-based microcapsules” can also encompass a shell made of a composite comprising a polyamide material and another material, for example a protein as defined in the present invention.
  • Polyamide-based microcapsules and “polyamide microcapsules” are used indifferently in the present invention.
  • Polyamide-based shell and “polyamide shell” are used indifferently in the present invention.
  • polyfunctional monomer it is meant a molecule that, as unit, reacts or binds chemically to form a polymer or a supramolecular polymer.
  • the polyfunctional monomer of the invention has at least two functional groups that are capable to react with or bind to functional groups of another component and/or are capable to polymerize to form a polymeric shell.
  • core-shell microcapsules preferably polyamide-based microcapsules with overall good performance in challenging bases could be obtained.
  • a first object of the invention is a core-shell microcapsule comprising: a core comprising a hydrophobic material, preferably a perfume oil, and a polymeric shell comprising a protein chosen in the group consisting of potato protein, chickpea protein, pea protein, algae protein, faba bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof.
  • the protein in the polymeric shell is cross-linked.
  • the protein in the polymeric shell is partially cross-linked. According to an embodiment, the protein in the polymeric shell is not cross-linked.
  • the polymeric shell comprises a polymerized polyfunctional monomer.
  • the core is an oil-based core.
  • the hydrophobic material according to the invention can be “inert” material like solvents or active ingredients.
  • hydrophobic material any hydrophobic material which forms a two-phase dispersion when mixed with water.
  • the hydrophobic material is typically liquid at about 20°C.
  • the hydrophobic material is a hydrophobic active ingredient.
  • the hydrophobic materials is an active ingredient, it is preferably chosen from the group consisting of flavors, flavor ingredients, perfumes, perfume ingredients, nutraceuticals, cosmetics, pest control agents, biocide actives and mixtures thereof.
  • the hydrophobic material comprises a phase change material (PCM).
  • the hydrophobic material comprises a mixture of a perfume with another ingredient selected from the group consisting of nutraceuticals, cosmetics, pest control agents and biocide actives.
  • the hydrophobic material comprises a mixture of biocide actives with another ingredient selected from the group consisting of perfumes, nutraceuticals, cosmetics, pest control agents.
  • the hydrophobic material comprises a mixture of pest control agents with another ingredient selected from the group consisting of perfumes, nutraceuticals, cosmetics, biocide actives.
  • the hydrophobic material comprises a perfume.
  • the hydrophobic material consists of a perfume.
  • the hydrophobic material consists of biocide actives.
  • the hydrophobic material consists of pest control agents.
  • perfume an ingredient or a composition that is a liquid at about 20°C.
  • said perfume oil can be a perfuming ingredient alone or a mixture of ingredients in the form of a perfuming composition.
  • a perfuming ingredient it is meant here a compound, which is used for the primary purpose of conferring or modulating an odor.
  • such an ingredient, to be considered as being a perfuming one must be recognized by a person skilled in the art as being able to at least impart or modify in a positive or pleasant way the odor of a composition, and not just as having an odor.
  • perfume oil also includes a combination of perfuming ingredients with substances which together improve, enhance or modify the delivery of the perfuming ingredients, such as perfume precursors, modulators, emulsions or dispersions, as well as combinations which impart an additional benefit beyond that of modifying or imparting an odor, such as long-lastingness, blooming, malodor counteraction, antimicrobial effect, microbial stability, pest control.
  • perfuming ingredients such as perfume precursors, modulators, emulsions or dispersions, as well as combinations which impart an additional benefit beyond that of modifying or imparting an odor, such as long-lastingness, blooming, malodor counteraction, antimicrobial effect, microbial stability, pest control.
  • perfuming ingredients present in the oil phase do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect.
  • these perfuming ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfurous heterocyclic compounds and essential oils (for example Thyme oil), and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery.
  • perfuming ingredients which are commonly used in perfume formulations, such as:
  • Aldehydic ingredients decanal, dodecanal, 2-methyl-undecanal, 10-undecenal, octanal, nonanal and/or nonenal;
  • Aromatic -herbal ingredients eucalyptus oil, camphor, eucalyptol, 5- methyltricyclo[6.2.1.0 2,7 ]undecan-4-one, l-methoxy-3 -hexanethiol, 2-ethyl-4,4- dimethyl-l,3-oxathiane, 2,2,7/8,9/10-tetramethylspiro[5.5]undec-8-en-l-one, menthol and/or alpha-pinene;
  • Citrus ingredients dihydromyrcenol, citral, orange oil, linalyl acetate, citronellyl nitrile, orange terpenes, limonene, l-p-menthen-8-yl acetate and/or l,4(8)-p-menthadiene;
  • Floral ingredients methyl dihydrojasmonate, linalool, citronellol, phenylethanol, 3-(4- tert-butylphenyl)-2-methylpropanal, hexylcinnamic aldehyde, benzyl acetate, benzyl salicylate, tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol, beta ionone, methyl 2- (methylamino)benzoate, (E)-3-methyl-4-(2,6,6-trimethyl-2-cyclohexen-l-yl)-3-buten- 2-one, (IE)- 1 -(2,6,6-trimethyl-2-cyclohexen- 1 -yl)- 1 -penten-3-one, 1 -(2,6,6-trimethyl- 1 ,3-cyclohexadien- 1 -yl)-2-buten- 1 -one, (2E)- 1 -(2,
  • Fruity ingredients gamma-undecalactone, 2,2,5-trimethyl-5-pentylcyclopentanone, 2- methyl-4-propyl-l,3-oxathiane, 4-decanolide, ethyl 2-methyl-pentanoate, hexyl acetate, ethyl 2-methylbutanoate, gamma-nonalactone, allyl heptanoate, 2- phenoxyethyl isobutyrate, ethyl 2-methyl-l,3-dioxolane-2-acetate, diethyl 1,4- cyclohexanedicarboxylate, 3-methyl-2-hexen-l-yl acetate, l-[3,3- dimethylcyclohexyl]ethyl [3-ethyl-2-oxiranyl]acetate and/or diethyl 1 ,4-cyclohexane dicarboxylate;
  • Woody ingredients l-[(lRS,6SR)-2,2,6-trimethylcyclohexyl]-3-hexanol, 3,3- dimethyl-5-[(lR)-2,2,3-trimethyl-3-cyclopenten-l-yl]-4-penten-2-ol, 3,4'- dimethylspiro[oxirane-2,9'-tricyclo[6.2.1.0 2 ’ 7 ]undec[4]ene, (1- ethoxyethoxy)cyclododecane, 2,2,9, 1 l-tetramethylspiro[5.5]undec-8-en-l-yl acetate,
  • ingredients e.g. amber, powdery spicy or watery: dodecahydro-3a,6,6,9a- tetramethyl-naphtho[2,l-b]furan and any of its stereoisomers, heliotropin, anisic aldehyde, eugenol, cinnamic aldehyde, clove oil, 3-(l,3-benzodioxol-5-yl)-2- methylpropanal, 7-methyl-2H-l ,5-benzodioxepin-3(4H)-one, 2,5,5-trimethyl- l,2,3,4,4a,5,6,7-octahydro-2-naphthalenol, 1-phenylvinyl acetate, 6-methyl-7-oxa-l- thia-4-azaspiro[4.4]nonane and/or 3-(3-isopropyl- 1 -phenyl)butanal.
  • ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds also known as properfume or profragrance.
  • suitable properfumes may include 4-(dodecylthio)-4- (2,6,6-trimethyl-2-cyclohexen-l-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-l- cyclohexen- 1 -yl)-2-butanone, 3 -(dodecylthio)- 1 -(2,6,6-trimethyl-3-cyclohexen- 1 -yl)- 1 - butanone, 2-(dodecylthio)octan-4-one, 2-phenylethyl oxo(phenyl)acetate, 3,7-dimethylocta- 2,6-dien-l-yl oxo(phenyl)acetate, (Z)-he
  • the perfuming ingredients may be dissolved in a solvent of current use in the perfume industry.
  • the solvent is preferably not an alcohol.
  • solvents are diethyl phthalate, isopropyl myristate, Abalyn® (rosin resins, available from Eastman), benzyl benzoate, ethyl citrate, triethyl citrate, limonene or other terpenes, or isoparaffins.
  • the solvent is very hydrophobic and highly sterically hindered, like for example Abalyn® or benzyl benzoate.
  • the perfume comprises less than 30% of solvent. More preferably the perfume comprises less than 20% and even more preferably less than 10% of solvent, all these percentages being defined by weight relative to the total weight of the perfume. Most preferably, the perfume is essentially free of solvent.
  • Preferred perfuming ingredients are those having a high steric hindrance and in particular those from one of the following groups: Group 1 : perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched Ci to C4 alkyl or alkenyl substituent;
  • Group 2 perfuming ingredients comprising a cyclopentane, cyclopentene, cyclopentanone or cyclopentenone ring substituted with at least one linear or branched C4 to Cs alkyl or alkenyl substituent;
  • Group 3 perfuming ingredients comprising a phenyl ring or perfuming ingredients comprising a cyclohexane, cyclohexene, cyclohexanone or cyclohexenone ring substituted with at least one linear or branched C5 to Cs alkyl or alkenyl substituent or with at least one phenyl substituent and optionally one or more linear or branched Ci to C3 alkyl or alkenyl substituents;
  • Group 4 perfuming ingredients comprising at least two fused or linked Cs and/or Ce rings
  • Group 5 perfuming ingredients comprising a camphor-like ring structure
  • Group 6 perfuming ingredients comprising at least one C7 to C20 ring structure
  • Group 7 perfuming ingredients having a logP value above 3.5 and comprising at least one tert-butyl or at least one trichloromethyl substitutent;
  • Group 1 2,4-dimethyl-3-cyclohexene-l-carbaldehyde (origin: Firmenich SA, Geneva, Switzerland), isocyclocitral, menthone, isomenthone, methyl 2,2-dimethyl-6-methylene- 1 -cyclohexanecarboxylate (origin: Firmenich SA, Geneva, Switzerland), nerone, terpineol, dihydroterpineol, terpenyl acetate, dihydroterpenyl acetate, dipentene, eucalyptol, hexylate, rose oxide, (S)-l,8-p-menthadiene-7-ol (origin: Firmenich SA, Geneva, Switzerland), l-p-menthene-4-ol, (lRS,3RS,4SR)-3-p-mentanyl acetate, (lR,2S,4R)-4,6,6-trimethyl-bicyclo[3,l,l]heptan-2-ol
  • Group 3 damascenes, l-(5,5-dimethyl-l-cyclohexen-l-yl)-4-penten-l-one (origin: Firmenich SA, Geneva, Switzerland), (l'R)-2-[2-(4'-methyl-3'-cyclohexen-r- yl)propyl]cyclopentanone, alpha-ionone, beta-ionone, damascenone, mixture of l-(5,5- dimethyl- 1 -cyclohexen- 1 -yl)-4-penten- 1 -one and 1 -(3 ,3 -dimethyl- 1 -cyclohexen- 1 -yl)-4- penten-l-one (origin: Firmenich SA, Geneva, Switzerland), l-(2,6,6-trimethyl-l- cyclohexen-l-yl)-2-buten-l-one (origin: Firmenich SA, Geneva, Switzerland), (1S,1'R)- [l
  • Group 4 Methyl cedryl ketone (origin: International Flavors and Fragrances, USA), a mixture of (lRS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1.0 2 ’ 6 ]dec-3-en-8-yl 2- methylpropanoate and (lRS,2SR,6RS,7RS,8SR)-tricyclo[5.2.1.0 2 ’ 6 ]dec-4-en-8-yl 2- methylpropanoate, vetyverol, vetyverone, l-(octahydro-2,3,8,8-tetramethyl-2- naphtalenyl)-l -ethanone (origin: International Flavors and Fragrances, USA), (5RS,9RS,10SR)-2,6,9,10-tetramethyl-l-oxaspiro[4.5]deca-3,6-diene and the (5RS,9SR,10RS) isomer, 6-ethyl-2,10,10-
  • Group 5 camphor, borneol, isobomyl acetate, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5- ene-2-carbaldehyde, pinene, camphene, 8-methoxycedrane, (8-methoxy-2,6,6,8- tetramethyl-tricyclo[5.3.1.0(l,5)]undecane (origin: Firmenich SA, Geneva, Switzerland), cedrene, cedrenol, cedrol, mixture of 9-ethylidene-3-oxatricyclo[6.2.1.0(2, 7)]undecan-4- one and 10-ethylidene-3-oxatricyclo[6.2.1.0 2,7 ]undecan-4-one (origin: Firmenich SA, Geneva, Switzerland), 3-methoxy-7,7-dimethyl-10-methylene-bicyclo[4.3.1]decane (origin: Firmenich SA, Geneva, Switzerland);
  • the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients selected from Groups 1 to 7, as defined above. More preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3 to 7, as defined above. Most preferably said perfume comprises at least 30%, preferably at least 50% of ingredients from Groups 3, 4, 6 or 7, as defined above.
  • the perfume comprises at least 30%, preferably at least 50%, more preferably at least 60% of ingredients having a logP above 3, preferably above 3.5 and even more preferably above 3.75.
  • the perfume used in the invention contains less than 10% of its own weight of primary alcohols, less than 15% of its own weight of secondary alcohols and less than 20% of its own weight of tertiary alcohols.
  • the perfume used in the invention does not contain any primary alcohols and contains less than 15% of secondary and tertiary alcohols.
  • the oil phase (or the oil-based core) comprises: 25-100wt% of a perfume oil comprising at least 15wt% of high impact perfume raw materials having a Log T ⁇ -4, and
  • odor threshold concentration of a chemical compound is determined in part by its shape, polarity, partial charges and molecular mass. For convenience, the odor threshold concentration is presented as the common logarithm of the threshold concentration, i.e., Log [Threshold] (“LogT”).
  • a “density balancing material” should be understood as a material having a density greater than 1.07 g/cm 3 and having preferably low or no odor.
  • the odor threshold concentration of a perfuming compound is determined by using a gas chromatograph (“GC”). Specifically, the gas chromatograph is calibrated to determine the exact volume of the perfume oil ingredient injected by the syringe, the precise split ratio, and the hydrocarbon response using a hydrocarbon standard of known concentration and chainlength distribution. The air flow rate is accurately measured and, assuming the duration of a human inhalation to last 12 seconds, the sampled volume is calculated. Since the precise concentration at the detector at any point in time is known, the mass per volume inhaled is known and hence the concentration of the perfuming compound. To determine the threshold concentration, solutions are delivered to the sniff port at the back-calculated concentration.
  • GC gas chromatograph
  • a panelist sniffs the GC effluent and identifies the retention time when odor is noticed. The average across all panelists determines the odor threshold concentration of the perfuming compound. The determination of odor threshold is described in more detail in C. Vuilleumier et al., Multidimensional Visualization of Physical and Perceptual Data Leading to a Creative Approach in Fragrance Development, Perfume & Flavorist, Vol. 33, September,, 2008, pages 54-61.
  • the high impact perfume raw materials having a Log T ⁇ -4 and density balancing material having a density greater than 1.07 g/cm 3 are described in WO2018115250, the content of which are included by reference.
  • the high impact perfume raw materials having a Log T ⁇ - 4 are selected from the group consisting of (+-)-l-methoxy-3-hexanethiol, 4-(4-hydroxy-l- phenyl)-2-butanone, 2-methoxy-4-(l -propenyl)- 1 -phenyl acetate, pyrazobutyle, 3- propylphenol, l-(3-methyl-l-benzofuran-2-yl)ethanone, 2-(3-phenylpropyl)pyridine, 1- (3,3/5 ,5-dimethyl- 1 -cyclohexen- 1 -yl)-4-penten- 1 -one , 1 -(5,5-dimethyl- 1 -cyclohexen- 1
  • perfume raw materials having a Log T ⁇ -4 are chosen in the group consisting of aldehydes, ketones, alcohols, phenols, esters lactones, ethers, epoxydes, nitriles and mixtures thereof.
  • perfume raw materials having a Log T ⁇ -4 comprise at least one compound chosen in the group consisting of alcohols, phenols, esters lactones, ethers, epoxydes, nitriles and mixtures thereof, preferably in amount comprised between 20 and 70% by weight based on the total weight of the perfume raw materials having a Log T ⁇ -4.
  • perfume raw materials having a Log T ⁇ -4 comprise between 20 and 70% by weight of aldehydes, ketones, and mixtures thereof based on the total weight of the perfume raw materials having a Log T ⁇ -4.
  • the remaining perfume raw materials contained in the oil-based core may have therefore a Log T>-4.
  • the perfume raw materials having a Log T>-4 are chosen in the group consisting of ethyl 2-methylbutyrate, (E)-3-phenyl-2-propenyl acetate, (+-)-6/8-sec-butylquinoline, (+-)-3-(l,3-benzodioxol-5-yl)-2-methylpropanal, verdyl propionate, l-(octahydro-2,3,8,8-tetramethyl-2-naphtalenyl)-l-ethanone, methyl 2- ((lRS,2RS)-3-oxo-2-pentylcyclopentyl)acetate, (+-)-(E)-4-methyl-3-decen-5-ol, 2,4- dimethyl-3-cyclohexene- 1 -carbaldehyde, 1 ,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, tetrahydro-4-methyl-2-(
  • the core comprises a perfume formulation comprising: 0 to 60 wt.% of a hydrophobic solvent (based on the total weight of the perfume formulation), 40 to 100 wt.% of a perfume oil (based on the total weight of the perfume formulation), wherein the perfume oil has at least two, preferably all of the following characteristics: o at least 35%, preferably at least 40%, preferably at least 50%, more preferably at least 60% of perfuming ingredients having a log P above 3, preferably above 3.5, o at least 20%, preferably at least 25%, preferably at least 30%, more preferably at least 40% of Bulky materials of groups 1 to 6, preferably 3 to 6 as herein defined and o at least 15%, preferably at least 20%, more preferably at least 25%, even more preferably at least 30% of high impact perfume materials having a Log T ⁇ -4, optionally, further hydrophobic active ingredients.
  • a perfume formulation comprising: 0 to 60 wt.% of a hydrophobic solvent (based on the total weight of the perfume formulation), 40
  • the perfume comprises 0 to 60 wt.% of a hydrophobic solvent.
  • the hydrophobic solvent is a density balancing material preferably chosen in the group consisting of benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylate, benzyl cinnamate, and mixtures thereof.
  • the hydrophobic solvent has Hansen Solubility Parameters compatible with entrapped perfume oil.
  • Hansen solubility parameter refers to a solubility parameter approach proposed by Charles Hansen used to predict polymer solubility and was developed around the basis that the total energy of vaporization of a liquid consists of several individual parts. To calculate the "weighted Hansen solubility parameter” one must combine the effects of (atomic) dispersion forces, (molecular) permanent dipole-permanent dipole forces, and (molecular) hydrogen bonding (electron exchange).
  • the weighted Hansen solubility parameter is calculated as (8D 2 + 8P 2 + 8H 2 ) 0 ' 5 , wherein 8D is the Hansen dispersion value (also referred to in the following as the atomic dispersion fore), 8P is the Hansen polarizability value (also referred to in the following as the dipole moment), and 8H is the Hansen Hydrogen-bonding ("h-bonding") value (also referred to in the following as hydrogen bonding).
  • h-bonding Hansen Hydrogen-bonding
  • Euclidean difference in solubility parameter between a fragrance and a solvent is Calculated which 8D S together, 8P S intersect, and 8H S rete, are the Hansen dispersion value, Hansen polarizability value, and Hansen h-bonding values of the solvent, respectively; and 8Dfr a grance, 8Pf r agrance, and 8Hfra g rance are the Hansen dispersion value, Hansen polarizability value, and Hansen h-bonding values of the fragrance, respectively.
  • the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force (8D) from 12 to 20, a dipole moment (8P) from 1 to 8, and a hydrogen bonding (8H) from 2.5 to 11.
  • the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force (8D) from 12 to 20, preferably from 14 to 20, a dipole moment (8P) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (8H) from 2.5 to 11, preferably from 4 to 11.
  • At least 90% of the perfume oil, preferably at least 95% of the perfume oil, most preferably at least of 98% of the perfume oil has at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force (8D) from 12 to 20, a dipole moment (8P) from 1 to 8, and a hydrogen bonding (8H) from 2.5 to 11.
  • the perfume oil and the hydrophobic solvent have at least two Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force (8D) from 12 to 20, preferably from 14 to 20, a dipole moment (8P) from 1 to 8, preferably from 1 to 7, and a hydrogen bonding (8H) from 2.5 to 11, preferably from 4 to 11.
  • the perfuming formulation comprises a fragrance modulator (that can be used in addition to the hydrophobic solvent when present or as substitution of the hydrophobic solvent when there is no hydrophobic solvent).
  • the fragrance modulator is defined as a fragrance material with i. a vapor pressure of less than 0.0008 Torr at 22°C; ii. a clogP of 3.5 and higher, preferable 4.0 and higher and more preferable 4.5 iii. at least two Hansen solubility parameters selected from a first group consisting of: an atomic dispersion force from 12 to 20, a dipole moment from 1 to 7, and a hydrogen bonding from 2.5 to 11 , iv.
  • Hansen solubility parameters selected from a second group consisting of: an atomic dispersion force from 14 to 20, a dipole moment from 1 to 8, and a hydrogen bonding from 4 to 11, when in solution with a compound having a vapor pressure range of 0.0008 to 0.08 Torr at 22°C.
  • ingredients can be listed as modulators but the list in not limited to the following materials: alcohol C12, oxacyclohexadec-12/13-en-2-one, 3-[(2',2',3'-trimethyl-3'-cyclopenten-r-yl)methoxy]-2-butanol, cyclohexadecanone, (Z)-4- cyclopentadecen-l-one, cyclopentadec anone, (8Z)-oxacycloheptadec-8-en-2-one, 2-[5-
  • the hydrophobic material is free of any active ingredient (such as perfume).
  • it comprises, preferably consists of hydrophobic solvents, preferably chosen in the group consisting of isopropyl myristate, tryglycerides (e.g.
  • biocide refers to a chemical substance capable of killing living organisms (e.g. microorganisms) or reducing or preventing their growth and/or accumulation. Biocides are commonly used in medicine, agriculture, forestry, and in industry where they prevent the fouling of, for example, water, agricultural products including seed, and oil pipelines.
  • a biocide can be a pesticide, including a fungicide, herbicide, insecticide, algicide, molluscicide, miticide and rodenticide; and/or an antimicrobial such as a germicide, antibiotic, antibacterial, antiviral, antifungal, antiprotozoal and/or antiparasite.
  • Pests refer to any living organism, whether animal, plant or fungus, which is invasive or troublesome to plants or animals, pests include insects notably arthropods, mites, spiders, fungi, weeds, bacteria and other microorganisms.
  • flavor oil it is meant here a flavoring ingredient or a mixture of flavoring ingredients, solvents or adjuvants of current use for the preparation of a flavoring formulation, i.e. a particular mixture of ingredients which is intended to be added to an edible composition or chewable product to impart, improve or modify its organoleptic properties, in particular its flavor and/or taste.
  • flavoring ingredients are well known to a person skilled in the art and their nature does not warrant a detailed description here, which in any case would not be exhaustive, the skilled flavorist being able to select them on the basis of his general knowledge and according to the intended use or application and the organoleptic effect it is desired to achieve. Many of these flavoring ingredients are listed in reference texts such as in the book by S.
  • the flavor is a mint flavor.
  • the mint is selected from the group consisting of peppermint and spearmint.
  • the flavor is a cooling agent or mixtures thereof.
  • the flavor is a menthol flavor.
  • Flavors that are derived from or based on fruits where citric acid is the predominant, naturally-occurring acid include but are not limited to, for example, citrus fruits (e.g. lemon, lime), limonene, strawberry, orange, and pineapple.
  • the flavors food is lemon, lime or orange juice extracted directly from the fruit.
  • Further embodiments of the flavor comprise the juice or liquid extracted from oranges, lemons, grapefruits, key limes, citrons, clementines, mandarins, tangerines, and any other citrus fruit, or variation or hybrid thereof.
  • the flavor comprises a liquid extracted or distilled from oranges, lemons, grapefruits, key limes, citrons, clementines, mandarins, tangerines, any other citrus fruit or variation or hybrid thereof, pomegranates, kiwifruits, watermelons, apples, bananas, blueberries, melons, ginger, bell peppers, cucumbers, passion fruits, mangos, pears, tomatoes, and strawberries.
  • the flavor comprises a composition that comprises limonene, in a particular embodiment, the composition is a citrus that further comprises limonene.
  • the flavor comprises a flavor selected from the group comprising strawberry, orange, lime, tropical, berry mix, and pineapple.
  • flavor includes not only flavors that impart or modify the smell of foods but include taste imparting or modifying ingredients.
  • the latter do not necessarily have a taste or smell themselves but are capable of modifying the taste that other ingredients provides, for instance, salt enhancing ingredients, sweetness enhancing ingredients, umami enhancing ingredients, bitterness blocking ingredients and so on.
  • suitable sweetening components may be included in the particles described herein.
  • a sweetening component is selected from the group consisting of sugar (e.g., but not limited to sucrose), a stevia component (such as but not limited to stevioside or rebaudioside A), sodium cyclamate, aspartame, sucralose, sodium saccharine, and Acesulfam K or mixtures thereof.
  • the polymeric shell comprises a material chosen in the group consisting of polyamide, polyurea, polyurethane, polyester, polyacrylate, polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, melamine and formaldehyde, melamine and urea, or melamine and glyoxal and mixtures thereof.
  • the polymeric material is a polyamide.
  • the polyamide material is obtained from the reaction between an acyl chloride and at least one amino compound (namely at least one amino-compound A), for example ethylene diamine (EDA).
  • at least one amino compound for example ethylene diamine (EDA).
  • the polyamide material is obtained from the reaction between an acyl chloride and at least two amino compounds (namely at least one amino-compound A and at least one amino-compound B), for example L-Lysine and ethylene diamine (EDA).
  • an acyl chloride namely at least one amino-compound A and at least one amino-compound B
  • EDA ethylene diamine
  • the polyamide is obtained from the reaction between an acyl chloride and at least three amino compounds (namely at least one aminocompound A, at least one amino-compound B and at least one amino-compound C), for example L-Lysine, ethylene diamine (EDA) and diethylene triamine (DETA).
  • aminocompound A at least one aminocompound A
  • amino-compound B at least one amino-compound B
  • amino-compound C for example L-Lysine, ethylene diamine (EDA) and diethylene triamine (DETA).
  • the amino-compound (A and/or B and/or C) can be chosen in the group consisting of cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl ester, cystine dialkyl ester hydrochloride, a xylylene diamine, 1 ,2-diaminocyclohexane, 1 ,4- diaminocyclohexane, poly etheramines, ethylene diamine, diethylene triamine, spermine, spermidine, polyamidoamine (PAMAM), guanidine carbonate, chitosan, tris-(2- aminoethyl) amine, 3-aminopropyltriethoxysilane, 1,4 Diaminobutane, 2,2Dimethyl-l,3- propanediamine, 1,3 -diaminopentane (Dytek EP diamine), 1,2 Diaminopropane, triethylenetetramine , 1,3-diaminoprop
  • At least one of the amino-compound is an aminoacid, preferably chosen in the group consisting of L-Lysine, L-Arginine, L-Histidine, L- Tryptophane, L-Serin, L-Glutamine, L-Threonine, L-Leucine, and mixtures thereof
  • the amino-compound (A and/or B and/or C) is chosen in the group consisting of a xylylene diamine, 1 ,2-diaminocyclohexane, 1 ,4-diaminocyclohexane, L-lysine, L-Lysine ethyl ester, polyetheramines (Jeffamine®), ethylene diamine, diethylene triamine, spermine, spermidine, polyamidoamine (PAM AM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, 1,4 Diaminobutane, 2,2Dimethyl-l,3-propanediamine, 1,3 -diaminopentane (Dytek EP diamine), 1,2 Diaminopropane, triethylenetetramine, an amine having a disulfide bond such as cyst
  • the acyl chloride has the following formula (I)
  • n is an integer varying between 1 and 8, preferably between 1 and 6, more preferably between 1 and 4, and wherein X is an (n+l)-valent C2 to C45 hydrocarbon group optionally comprising at least one group selected from (i) to (xi), more particularly selected from (i) to (vi),
  • R is a hydrogen atom or an alkyl group such as a methyl or an ethyl group, preferably a hydrogen atom.
  • hydrocarbon group consists of hydrogen and carbon atoms and can be in the form of an aliphatic hydrocarbon, i.e. linear or branched saturated hydrocarbon (e.g. alkyl group), a linear or branched unsaturated hydrocarbon (e.g. alkenyl or alkynil group), a saturated cyclic hydrocarbon (e.g. cycloalkyl) or an unsaturated cyclic hydrocarbon (e.g. cycloalkenyl or cycloalkynyl), or can be in the form of an aromatic hydrocarbon, i.e. aryl group, or can also be in the form of a mixture of said type of groups, e.g.
  • a specific group may comprise a linear alkyl, a branched alkenyl (e.g. having one or more carbon-carbon double bonds), a (poly)cycloalkyl and an aryl moiety, unless a specific limitation to only one type is mentioned.
  • a group when a group is mentioned as being in the form of more than one type of topology (e.g. linear, cyclic or branched) and/or being saturated or unsaturated (e.g. alkyl, aromatic or alkenyl), it is also meant a group which may comprise moieties having any one of said topologies or being saturated or unsaturated, as explained above.
  • a group when a group is mentioned as being in the form of one type of saturation or unsaturation, (e.g. alkyl), it is meant that said group can be in any type of topology (e.g. linear, cyclic or branched) or having several moieties with various topologies.
  • hydrocarbon group optionally comprising ...” it is meant that said hydrocarbon group optionally comprises heteroatoms to form ether, thioether, amine, nitrile or carboxylic acid groups and derivatives (including for example esters, acids, amide). These groups can either substitute a hydrogen atom of the hydrocarbon group and thus be laterally attached to said hydrocarbon, or substitute a carbon atom (if chemically possible) of the hydrocarbon group and thus be inserted into the hydrocarbon chain or ring.
  • the acyl chloride is chosen from the group consisting of benzene-l,3,5-tricarbonyl trichloride (trimesoyl trichloride), benzene- 1,2,4- tricarbonyl trichloride, benzene- 1,2, 4, 5 -tetracarbonyl tetrachloride, cyclohexane-1,3,5- tricarbonyl trichloride, isophthalyol dichloride, diglycolyl dichloride, terephthaloyl chloride, fumaryl dichloride, adipoyl chloride, succinic dichloride, propane- 1, 2, 3-tricarbonyl trichloride, cyclohexane- 1,2, 4, 5-tetracarbonyl tetrachloride, 2,2'-disulfanediyldisuccinyl dichloride, 2-(2- chloro-2-oxo-ethyl)sulfanyl
  • the acyl chloride is chosen from the group consisting of benzene- 1,2, 4-tricarbonyl trichloride, benzene- 1,2, 4, 5-tetracarbonyl tetrachloride, cyclohexane-l,3,5-tricarbonyl trichloride, isophthalyol dichloride, diglycolyl dichloride, terephthaloyl chloride, fumaryl dichloride, adipoyl dichloride, succinic dichloride, propane-1, 2, 3-tricarbonyl trichloride, cyclohexane- 1,2, 4, 5-tetracarbonyl tetrachloride, 2,2'- disulfanediyldisuccinyl dichloride, 2-(2-chloro-2-oxo-ethyl)sulfanylbutanedioyl dichloride, (4-chloro-4-oxobutanoyl)-L-glu
  • the acyl chloride is chosen from the group consisting of fumaryl dichloride, adipoyl dichloride, succinic dichloride, propane- 1, 2, 3-triyl tris(4-chloro-4-oxobutanoate), propane- 1,2-diyl bis(4-chloro-4-oxobutanoate), and mixtures thereof.
  • the acyl chloride is a mixture of acyl chlorides.
  • the weight ratio between acyl chloride and the hydrophobic material is preferably comprised between 0.01 and 0.09, more preferably between 0.02 and 0.07.
  • the acyl chloride is used in an amount comprised between 1.7 and 7%, preferably between 2.5 and 5 % by weight based on the total weight of the hydrophobic material.
  • the protein is chosen in the group consisting of potato protein, chickpea protein, pea protein and mixtures thereof.
  • the core-shell microcapsule comprises: a core comprising a hydrophobic material, preferably a perfume oil, and a polyamide shell comprising the reaction product between one acyl chloride and at least two amino-compounds, preferably L-Lysine and ethylene diamine, wherein the polyamide shell comprises a potato protein.
  • the core-shell microcapsule comprises: a core comprising a hydrophobic material, preferably a perfume oil, and a polyamide shell comprising the reaction product between one acyl chloride and at least two amino-compounds, preferably L-Lysine and ethylene diamine, wherein the polyamide shell comprises a chickpea protein.
  • the core-shell microcapsule comprises: a core comprising a hydrophobic material, preferably a perfume oil, and a polyamide shell comprising the reaction product between one acyl chloride and at least two amino-compounds, preferably L-Lysine and ethylene diamine, wherein the polyamide shell comprises a pea protein.
  • the polyamide shell can comprise the reaction product between one acyl chloride and at least three amino-compounds, preferably L-Lysine, ethylene diamine and ethylene tri amine.
  • Another object of the invention is a polyamide-based core-shell microcapsule or a polyamide-based core-shell microcapsule slurry comprising at least one microcapsule, the microcapsule comprising: a core comprising a hydrophobic material, preferably a perfume, and a polyamide-based shell comprising a reaction product of
  • an acyl chloride in an amount comprised between 5 and 98%, preferably between 20 and 98%, more preferably between 30 and 85% w/w
  • an amino compound A in an amount comprised between 1% and 50% w/w, preferably between 7 and 40% w/w;
  • a protein chosen in the group consisting of potato protein, chickpea protein, pea protein, algae protein, faba bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof, in an amount comprised between 0.1 and 90% w/w, preferably between 0.1 and 75% w/w, more preferably between 1 and 70% w/w, based on the total weight of the shell.
  • the polyamide-based shell comprises a reaction product of:
  • an acyl chloride in an amount comprised between 5 and 98%, preferably between 5 and 40%, more preferably between 5 and 30% w/w
  • an amino compound A in an amount comprised between 1% and 50% w/w, preferably between 7 and 40% w/w;
  • the shell comprises the protein in an amount comprised between 1 and 80% w/w, more preferably between 10 and 75% w/w, even more preferably between 30 and 70% w/w based on the total weight of the shell.
  • the shell material is a biodegradable material.
  • the shell has a biodegradability of at least 40%, preferably at least 45%, 50%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98%, within 60 days according to OECD301F.
  • the core-shell microcapsule has a biodegradability of at least 40 %, preferably at least 60 %, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD301F.
  • the core- shell microcapsule including all components, such as the core, shell and optionally coating may have a biodegradability of at least 40 %, preferably at least 60 %, preferably at least 65%, 70%, 75%, 80%, 85%, 90%, 95% or 98% within 60 days according to OECD301F.
  • the oil core preferably perfume oil
  • OECD301F is a standard test method on the biodegradability from the Organization of Economic Co-operation and Development.
  • a typical method for extracting the shell for measuring the biodegradability is disclosed in Gasparini and all in Molecules 2020, 25,718.
  • the microcapsule has a stability or chemical stability of not more than 50%, preferably not more than 40%, preferably not more than 35%, preferably more than 30%.
  • the stability or chemical stability of the microcapsules being determined as not more than 50%, preferably not more than 40%, preferably not more than 35%, preferably not more than 30%, of the perfume leaking out of the microcapsules when incorporated in a consumer product for a particular storage time and temperature, with the microcapsules being stable after 15 days storage at 37° C, more preferably after 30 days storage at 37°C preferably in fabric softeners, liquid detergents, body washes, deodorants or antiperspirants, for at least 2 weeks storage at 40° C in body lotions, shampoos or hair conditioners.
  • microcapsule shows preferably a rubbing effect detectable on fresh samples, and preferably after 15 days of storage in application at 37°C, even more preferably after 30 days at 37°C.
  • Protein used in the present invention is a plant-protein or a plant-based protein.
  • Plantprotein or “plant-based protein” are used indifferently in the present invention.
  • the protein is chosen in the group consisting of potato protein, chickpea protein, pea protein, algae protein, faba bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof.
  • Potato proteins are typically extracted from potato tuber (Solanum tuberosum). According to an embodiment, the potato protein is a native potato protein and preferably comprises or consisting of patatin.
  • the solubility of the protein, preferably potato protein is greater than 10%. According to an embodiment, the solubility of the protein, preferably potato protein, is greater than 20%. According to an embodiment, the solubility of the protein, preferably potato protein, is greater than 30%. According to an embodiment, the solubility of the protein, preferably potato protein, is greater than 40%. According to an embodiment, the solubility of the protein, preferably potato protein, is greater than 50%. According to an embodiment, the solubility of the protein, preferably potato protein, is greater than 60%. According to an embodiment, the solubility of the protein, preferably potato protein, is greater than 70%. According to an embodiment, the solubility of the protein, preferably potato protein, is greater than 80%. According to an embodiment, the solubility of the protein, preferably potato protein, is greater than 90%.
  • the above solubilities are given in water at room temperature (typically 20°C) and preferably at native pH.
  • the protein used in this invention may be native, partially or completely denaturated by any suitable method.
  • Denaturation is a process which modify the conformational structure of a protein by unfolding, i.e., it involves the disruption and possible destruction of both the secondary and tertiary structures of the protein. Indeed, denaturation implicates the breaking of many of the weak linkages, or bonds (e.g., hydrogen bonds), within a protein molecule that are responsible for the highly ordered structure of the protein in its native state. Denaturation is reversible (the proteins can regain their native state when the denaturating influence is removed) or irreversible.
  • Denaturation can be brought about in various ways. Proteins can be denatured by exposure to temperature, radiation or mechanical stress including shear, changes in pH (treatment with a base or an acid), treatment with oxidizing or reducing agents, inorganic salt, certain organic solvents, chaotropic agents (i.e, compounds having a positive chaotropic value - kJ Kg 1 mole on the Hallsworth Scale - such as guanidine salts - e.g., guanidine carbonate, guanidine hydrochloride urea, calcium chloride, n-butanol, ethanol, lithium perchlorate, lithium acetate, magnesium chloride, phenol, 2-propanol, sodium dodecyl sulfate, thiourea).
  • chaotropic agents i.e, compounds having a positive chaotropic value - kJ Kg 1 mole on the Hallsworth Scale - such as guanidine salts - e.g., gu
  • the protein used in this invention can also be derivatized or modified (e.g., derivatized or chemically modified).
  • the protein can be modified by covalently attaching sugars, lipids, peptides or chemical groups such as phosphates or methyl.
  • the protein before use, can be treated by a heat treatment (typically around 90°C) with or without the presence of a salt (for example CaCh or NaCl).
  • a heat treatment typically around 90°C
  • a salt for example CaCh or NaCl
  • the microcapsule comprises an outer coating, wherein the outer coating comprises a coating material selected from the group consisting of a non-ionic polysaccharide, a cationic polymer, a polysuccinimide derivative (as described for instance in WO2021185724) and mixtures thereof to form an outer coating to the microcapsule.
  • the outer coating comprises a coating material selected from the group consisting of a non-ionic polysaccharide, a cationic polymer, a polysuccinimide derivative (as described for instance in WO2021185724) and mixtures thereof to form an outer coating to the microcapsule.
  • Non-ionic polysaccharide polymers are well known to a person skilled in the art and are described for instance in W02012/007438 page 29, lines 1 to 25 and in WO2013/026657 page 2, lines 12 to 19 and page 4, lines 3 to 12.
  • Preferred non-ionic polysaccharides are selected from the group consisting of locust bean gum, xyloglucan, guar gum, hydroxypropyl guar, hydroxypropyl cellulose and hydroxypropyl methyl cellulose.
  • Cationic polymers are well known to a person skilled in the art.
  • Preferred cationic polymers have cationic charge densities of at least 0.5 meq/g, more preferably at least about 1.5 meq/g, but also preferably less than about 7 meq/g, more preferably less than about 6.2 meq/g.
  • the cationic charge density of the cationic polymers may be determined by the Kjeldahl method as described in the US Pharmacopoeia under chemical tests for Nitrogen determination.
  • the preferred cationic polymers are chosen from those that contain units comprising primary, secondary, tertiary and/or quaternary amine groups that can either form part of the main polymer chain or can be borne by a side substituent directly connected thereto.
  • the weight average (Mw) molecular weight of the cationic polymer is preferably between 10,000 and 3.5M Dalton, more preferably between 50,000 and 1.5M Dalton.
  • Mw weight average molecular weight
  • cationic polymers based on acrylamide, methacrylamide, N- vinylpyrrolidone, quaternized N,N-dimethylaminomethacrylate, diallyldimethylammonium chloride, quaternized vinylimidazole (3 -methyl- 1 -vinyl- lH-imidazol-3-ium chloride), vinylpyrrolidone, acrylamidopropyltrimonium chloride, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride or polygalactomannan 2- hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride.
  • copolymers shall be selected from the group consisting of polyquatemium-5, polyquatemium-6, polyquaternium-7, polyquatemiumlO, polyquatemium- 11 , polyquaternium-16, polyquatemium-22, polyquatemium-28, polyquatemium-43, polyquatemium-44, polyquatemium-46, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride or polygalactomannan 2-hydroxypropyltrimethylammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride.
  • Salcare® SC60 cationic copolymer of acrylamidopropyltrimonium chloride and acrylamide, origin: BASF
  • Luviquat® such as the PQ UN, FC 550 or Style (polyquatemium- 11 to 68 or quatemized copolymers of vinylpyrrolidone origin: BASF), or also the Jaguar® (C13S or C17, origin Rhodia).
  • an amount of polymer described above comprised between about 0% and 5% w/w, or even between about 0.1% and 2% w/w, percentage being expressed on a w/w basis relative to the total weight of the slurry. It is clearly understood by a person skilled in the art that only part of said added polymers will be incorporated into/deposited on the microcapsule shell.
  • the microcapsule of the present invention comprises a mineral layer.
  • the mineral layer preferably comprises a material chosen in the group consisting of iron oxides, iron oxyhydroxide, titanium oxides, zinc oxides, calcium carbonates, calcium phosphates, barium salt, strontium salt, magnesium salt, and mixtures thereof and mixtures thereof.
  • the microcapsule slurry can comprise auxiliary ingredients selected from the group of thickening agents/rheology modifiers, antimicrobial agents, opacity-building agents, mica particles, salt, pH stabilizers/buffering ingredients, preferably in an amount comprised between 0 and 15% by weight based on the total weight of the slurry.
  • the microcapsule slurry of the invention comprises additional free (i.e non-encapsulated) perfume, preferably in an amount comprised between 5 and 50% by weight based on the total weight of the slurry.
  • Another object of the invention is a solid particle comprising: a carrier material, preferably a polymeric carrier material chosen in the group consisting of polyvinyl acetate, polyvinyl alcohol, dextrins, natural or modified starch, vegetable gums, pectins, xanthans, alginates, carragenans, cellulose derivatives and mixtures thereof, and microcapsules as defined above entrapped in said carrier material, and optionally free perfume entrapped in said carrier material.
  • a carrier material preferably a polymeric carrier material chosen in the group consisting of polyvinyl acetate, polyvinyl alcohol, dextrins, natural or modified starch, vegetable gums, pectins, xanthans, alginates, carragenans, cellulose derivatives and mixtures thereof, and microcapsules as defined above entrapped in said carrier material, and optionally free perfume entrapped in said carrier material.
  • Solid particle as defined above and microcapsule powder can be used indifferently in the present invention.
  • Another object of the invention is a process for preparing a core-shell microcapsule slurry comprising the step of: a) Preparing an oil phase comprising a hydrophobic material, preferably a perfume to form an oil phase; b) Dispersing the oil phase obtained in step a) into a water phase to form an oil-in water emulsion; c) Performing a curing step to form microcapsules in the form of a slurry; wherein a polyfunctional monomer is added in the oil phase and/or in the water phase, and wherein a protein chosen in the group consisting of potato protein, chickpea protein, pea protein, algae protein, faba bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof is added in the oil phase and/or in the water phase.
  • the polyfunctional monomer is chosen in the group consisting of at least one acyl chloride, a polyisocyanate, poly anhydride (such as poly maleic anhydride), poly epoxide, acrylate monomers, poly alkoxy silane, and mixtures thereof.
  • the polyfunctional monomer is a polyisocyanate having at least two isocyanate functional groups.
  • Suitable polyisocyanates used according to the invention can include aromatic polyisocyanate, aliphatic polyisocyanate and mixtures thereof.
  • Said polyisocyanate comprises at least 2, preferably at least 3 but may comprise up to 6, or even only 4, isocyanate functional groups.
  • a triisocyanate (3 isocyanate functional group) is used.
  • said polyisocyanate is an aromatic polyisocyanate.
  • aromatic polyisocyanate is meant here as encompassing any polyisocyanate comprising an aromatic moiety. Preferably, it comprises a phenyl, a toluyl, a xylyl, a naphthyl or a diphenyl moiety, more preferably a toluyl or a xylyl moiety.
  • Preferred aromatic polyisocyanates are biurets, polyisocyanurates and trimethylol propane adducts of diisocyanates, more preferably comprising one of the above-cited specific aromatic moieties.
  • the aromatic polyisocyanate is a polyisocyanurate of toluene diisocyanate (commercially available from Bayer under the tradename Desmodur® RC), a trimethylol propane-adduct of toluene diisocyanate (commercially available from Bayer under the tradename Desmodur® L75), a trimethylol propane-adduct of xylylene diisocyanate (commercially available from Mitsui Chemicals under the tradename Takenate® D-110N).
  • the aromatic polyisocyanate is a trimethylol propane- adduct of xylylene diisocyanate.
  • said polyisocyanate is an aliphatic polyisocyanate.
  • aliphatic polyisocyanate is defined as a polyisocyanate which does not comprise any aromatic moiety.
  • Preferred aliphatic polyisocyanates are a trimer of hexamethylene diisocyanate, a trimer of isophorone diisocyanate, a trimethylol propane-adduct of hexamethylene diisocyanate (available from Mitsui Chemicals) or a biuret of hexamethylene diisocyanate (commercially available from Bayer under the tradename Desmodur® N 100), among which a biuret of hexamethylene diisocyanate is even more preferred.
  • the at least one polyisocyanate is in the form of a mixture of at least one aliphatic polyisocyanate and of at least one aromatic polyisocyanate, both comprising at least two or three isocyanate functional groups, such as a mixture of a biuret of hexamethylene diisocyanate with a trimethylol propane- adduct of xylylene diisocyanate, a mixture of a biuret of hexamethylene diisocyanate with a polyisocyanurate of toluene diisocyanate and a mixture of a biuret of hexamethylene diisocyanate with a trimethylol propane-adduct of toluene diisocyanate.
  • it is a mixture of a biuret of hexamethylene diisocyanate with a trimethylol propane- adduct of xylylene diisocyanate.
  • the molar ratio between the aliphatic polyisocyanate and the aromatic polyisocyanate is ranging from 80:20 to 10:90.
  • the polyfunctional monomer is an acyl chloride.
  • the process comprises the steps of: a) Preparing an oil phase comprising an acyl chloride and a hydrophobic material, preferably a perfume to form an oil phase; b) Dispersing the oil phase obtained in step a) into a water phase to form an oil-in water emulsion; c) Performing a curing step to form microcapsules in the form of a slurry; wherein at least one amino-compound is added in the water phase before the formation of the oil- in-water emulsion and/or in the oil-in water emulsion obtained after step b), and wherein a protein chosen in the group consisting of potato protein, chickpea protein, pea protein, algae protein, faba bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof is added in the oil phase and/or in the water phase.
  • microcapsules according to the invention also apply to the process according to the invention. This particularly applies to the hydrophobic material, the protein, the acyl chloride, the amino compound(s).
  • a protein chosen in the group consisting of potato protein, chickpea protein, pea protein, algae protein, faba bean protein, barley protein, oat protein, wheat gluten protein, lupin protein, and mixtures thereof is added in the oil phase and/or in the water phase. According to a particular embodiment, the protein is added in the oil phase.
  • the protein When added in the oil phase, the protein can be pre-dispersed (or pre-dissolved) in an inert solvent or any inert perfumery solvent/ingredient such as such as benzyl benzoate, triethyl citrate, ethyl acetate, vegetable oil (such as sunflower oil), hexyl salicylate, Neobee (caprylic/capric triglyceride), isopropyl myristate, try glycerides, D-limonene, silicone oil, mineral oil, benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylate, benzyl cinnamate and mixtures thereof, or can be mixed to the active ingredient, preferably comprising a perfume oil.
  • the protein is preferably used in an amount comprise
  • the protein defined in the present invention acts as a stabilizer.
  • a stabilizer can be further added in the water phase and/or the oil phase to form the emulsion.
  • the stabilizer is a colloidal stabilizer.
  • stabilizer it is meant a compound capable to stabilize oil/water interface as an emulsion typically by lowering the interfacial tension between the oil phase and the water phase.
  • Stabilizer or “emulsifier” can be used indifferently in the present invention.
  • the stabilizer is a colloidal stabilizer.
  • the colloidal stabilizer can be a polymeric emulsifier (standard emulsion), a surfactant, or solid particles (Pickering emulsion).
  • Molecular emulsifier and “polymeric emulsifier” are used indifferently in the present invention.
  • polymeric emulsifier By “polymeric emulsifier”, it meant an emulsifier having both a polar group with an affinity for water (hydrophilic) and a nonpolar group with an affinity for oil (hydrophobic). The hydrophilic part will dissolve in the water phase and the hydrophobic part will dissolve in the oil phase providing a film around droplets.
  • surfactant it meant a non-polymeric substance with a polar and a non-polar group.
  • the stabilizer is chosen in the group consisting of inorganic particles, polymeric emulsifier such as polysaccharides, proteins, glycoproteins, and mixtures thereof.
  • the stabilizer when it is solid particles, it can be chosen in the group consisting of calcium phosphate, silica, silicates, titanium dioxide, aluminium oxide, zinc oxide, iron oxide, mica, kaolin, montmorillonite, laponite, bentonite, perlite, dolomite, diatomite, vermiculite, hectorite, gibbsite, illite, kaolinite, aluminosilicates, gypsum, bauxite, magnesite, talc, magnesium carbonate, calcium carbonate, diatomaceous earth and mixtures thereof.
  • the stabilizer is a biopolymer.
  • the stabilizer is the polymer as defined above.
  • biopolymers it is meant biomacromolecules produced by living organisms. Biopolymers are characterized by molecular weight distributions ranging from 1,000 (1 thousand) to 1,000,000,000 (1 billion) Daltons. These macromolecules may be carbohydrates (sugar based) or proteins (amino-acid based) or a combination of both (gums) and can be linear or branched.
  • the colloid stabilizer is chosen in the group consisting of gum Arabic, modified starch, polyvinyl alcohol, polyvinylpyrolidone (PVP), acrylamide copolymer, inorganic particles, protein such as soy protein, rice protein, whey protein, white egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudocollagen, silk protein, sericin powder, and mixtures thereof.
  • PVP polyvinylpyrolidone
  • acrylamide copolymer inorganic particles
  • protein such as soy protein, rice protein, whey protein, white egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, pseudocollagen, silk protein, sericin powder, and mixtures thereof.
  • the stabilizer When added in the oil phase, the stabilizer can be pre-dispersed (or pre-dissolved) in an inert solvent or any inert perfumery solvent/ingredient such as such as benzyl benzoate, triethyl citrate, ethyl acetate, vegetable oil (such as sunflower oil), hexyl salicylate, Neobee (caprylic/capric triglyceride), isopropyl myristate, try glycerides, D-limonene, silicone oil, mineral oil, benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylate, benzyl cinnamate and mixtures thereof, or can be mixed to the active ingredient, preferably comprising a perfume oil.
  • the stabilizer and acyl chloride can be premixed and can be heated at a temperature between for example 10 and 80°C before mixing with the hydrophobic material, preferably comprising a perfume oil.
  • the colloidal stabilizer When added in the water phase, it is preferably chosen in the group consisting of gum Arabic, modified starch, polyvinyl alcohol, polyvinylpyrolidone (PVP), acrylamide copolymer, inorganic particles, protein such as soy protein, rice protein, whey protein, white egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, Pseudocollagen, Silk protein, sericin powder, and mixtures thereof.
  • PVP polyvinylpyrolidone
  • acrylamide copolymer inorganic particles
  • protein such as soy protein, rice protein, whey protein, white egg albumin, sodium caseinate, gelatin, bovine serum albumin, hydrolyzed soy protein, hydrolyzed sericin, Pseudocollagen, Silk protein, sericin powder, and mixtures thereof.
  • the dispersion can comprise between about 0.01% and 3.0% of at least stabilizer, preferably colloidal stabilizer, percentage being expressed on a w/w basis relative to the total weight of the oil-in- water emulsion as obtained after step b).
  • the dispersion can comprise between about 0.05% and 2.0%, preferably between 0.05 and 1% of at least a stabilizer, preferably colloidal stabilizer.
  • the dispersion can comprise between about 0.1% and 1.6%, preferably between 0.1% and 0.8% by weight of at least a stabilizer, preferably colloidal stabilizer,
  • acyl chloride used in the process can be defined as it has been previously described for the microcapsules.
  • the weight ratio between acyl chloride and the hydrophobic material is preferably comprised between 0.01 and 0.09, more preferably between 0.02 and 0.07.
  • the acyl chloride is used in an amount comprised between 1.7 and 7%, preferably between 2.5 and 5 % by weight based on the total weight of the hydrophobic material.
  • the acyl chloride can be dissolved (or dispersed) directly in the perfume oil or can be predispersed (or pre-dissolved) in an inert solvent or any inert perfumery solvent/ingredient such as benzyl benzoate, triethyl citrate, ethyl acetate, vegetable oil (such as sunflower oil), hexyl salicylate, Neobee (caprylic/capric triglyceride), isopropyl myristate, try glycerides, D- limonene, silicone oil, mineral oil, benzyl salicylate, benzyl benzoate, cyclohexyl salicylate, benzyl phenylacetate, phenylethyl phenylacetate, triacetin, ethyl citrate, methyl and ethyl salicylate, benzyl cinnamate and mixtures thereof, before mixing with the perfume oil.
  • any inert perfumery solvent/ingredient such
  • the water phase comprises a base preferably chosen in the group consisting of sodium carbonate, sodium bicarbonate, sodium hydroxide, guanidine carbonate, triethanolamine and mixtures thereof.
  • the base can also be added in the oil-in-water emulsion.
  • the base is not an amino compound.
  • the water phase comprises a base preferably chosen in the group consisting of sodium carbonate, sodium bicarbonate, sodium hydroxide, and mixtures thereof.
  • the base can be added in an amount comprise between 0.01 and 1.5%, preferably between 0.01 and 0.7% by weight based on the total weight of the water phase.
  • At least one amino-compound (amino-compound A) is added in the water phase before the formation of the oil- in- water emulsion and/or in the oilin water emulsion obtained after step b).
  • the molar ratio between the functional groups NH2 of the at least amino compound and the functional groups COCI of the acyl chloride is comprised between 0.2 and 3, preferably from 0.5 to 2, more preferably between 0.2 and 1.
  • at least one additional amino-compound (aminocompound B) is added in the water phase before the formation of the oil-in-water emulsion and/or in the oil-in water emulsion obtained after step b).
  • At least one additional amino-compound to aminocompounds A and B is added in the water phase before the formation of the oil-in-water emulsion and/or in the oil-in water emulsion obtained after step b).
  • the amino-compound (A and/or B and/or C) is chosen in the group consisting of a xylylene diamine, 1 ,2-diaminocyclohexane, 1 ,4-diaminocyclohexane, L-lysine, L-Lysine ethyl ester, polyetheramines (Jeffamine®), ethylene diamine, diethylene triamine, spermine, spermidine, polyamidoamine (PAM AM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, L-arginine, 1,4 Diaminobutane, 2,2Dimethyl-l,3-propanediamine, 1,3 -diaminopentane (Dytek EP diamine), 1,2 Diaminopropane, triethylenetetramine , an amine having a disulfide bond such as
  • the amino-compound (A and/or B and/or C) is chosen in the group consisting of cystamine, cystamine hydrochloride, cystine, cystine hydrochloride, cystine dialkyl ester, cystine dialkyl ester hydrochloride, a xylylene diamine, 1,2- diaminocyclohexane, 1 ,4-diaminocyclohexane, poly etheramines, ethylene diamine, diethylene triamine, spermine, spermidine, polyamidoamine (PAM AM), guanidine carbonate, chitosan, tris-(2-aminoethyl)amine, 3-aminopropyltriethoxysilane, 1,4 Diaminobutane, 2,2Dimethyl- 1,3 -propanediamine, 1,3 -diaminopentane (Dytek EP diamine), 1,2 Diaminopropane, triethylenetetramine , 1,3-diamin
  • At least one amino-compound (amino-compound A) is added in the water phase before the formation of the oil- in-water emulsion and/or in the oil-in water emulsion obtained after step b).
  • At least one amino-compound (amino-compound A) preferably an amino-acid, more preferably L-Lysine is added in the water phase before the formation of the oil- in-water emulsion and at least one amino-compound (amino-compound B) or at least two amino-compounds (amino-compound B and amino-compound C) are added in the water phase before the formation of the oil- in-water emulsion and/or in the oil-in water emulsion obtained after step b), wherein the amino- compound B is preferably ethylene diamine and wherein the amino-compound C is preferably diethylene triamine.
  • a base can also be added in the water phase and/or in the oil-in-water emulsion.
  • the molar ratio between the functional groups NH2 of ethylene diamine and diethylene triamine (EDA + DETA) and the functional groups COCI of the acyl chloride is comprised between 0.2 and 3, preferably from 0.5 to 2, more preferably between 0.2 and 1.
  • a multivalent salt (such as calcium chloride, magnesium chloride, zinc chloride, iron trichloride) is added after step b), before or during step c).
  • a carbohydrate is added in the water phase and/or in the oil phase.
  • carboxylate it should be understood a polymer or an oligomer having a number of units greater than 2.
  • the carbohydrate, the amino-compound A and the amino compound B are different components.
  • At least one carbohydrate is added in the oil phase and/or in the water phase.
  • the carbohydrate is not a polyphenol.
  • the carbohydrate is not a functionalized carbohydrate.
  • the carbohydrate is a polysaccharide.
  • the polysaccharide is an anionic polysaccharide.
  • the polysaccharide is added in the water phase.
  • the polysaccharide is preferably chosen in the group consisting of anionic salt of alginic acid, preferably alginic acid sodium salt, pectin, lignin, anionic modified starch, carboxymethylcellulose and mixtures thereof.
  • the carbohydrate is an anionic salt of alginic acid, preferably alginic acid sodium salt.
  • Alginic acid sodium salt and “sodium alginate” can be used indifferently. According to a particular embodiment, the carbohydrate is used in an amount comprised between 0.1 and 5%, preferably between 0.5 and 1.1% by weight based on the total weight of the water phase.
  • the microcapsules of the invention can be used in combination with a second type of microcapsules.
  • Another object of the invention is a microcapsule delivery system comprising: the microcapsules of the present invention as a first type of microcapsule, and a second type of microcapsules, wherein the first type of microcapsule and the second type of microcapsules differ in their hydrophobic material and/or their wall material and/or in their coating material.
  • the microcapsule delivery system is in the form of a slurry.
  • the wall of the second type of microcapsules can vary.
  • the polymer shell of the second type of microcapsules comprises a material selected from the group consisting of polyurea, polyurethane, polyamide, poly hydroxy alkanoates, polyacrylate, polyesters, poly aminoesters, polyepoxides, polysiloxane, polycarbonate, polysulfonamide, urea formaldehyde, melamine formaldehyde resin, melamine formaldehyde resin cross-linked with polyisocyanate or aromatic polyols, melamine urea resin, melamine glyoxal resin, gelatin/ gum arabic shell wall, and mixtures thereof.
  • the second type of microcapsule can comprises an oil-based core comprising a hydrophobic active, preferably perfume, and a composite shell comprising a first material and a second material, wherein the first material and the second material are different, the first material is a coacervate, the second material is a polymeric material.
  • the weight ratio between the first material and the second material is comprised between 50:50 and 99.9:0.1.
  • the coacervate comprises a first poly electrolyte, preferably selected among proteins (such as gelatin), polypeptides or polysaccharides (such as chitosan), most preferably Gelatin and a second polyelectrolyte, preferably alginate salts, cellulose derivatives guar gum, pectinate salts, carrageenan, polyacrylic and methacrylic acid or xanthan gum, or yet plant gums such as acacia gum (Gum Arabic), most preferably Gum Arabic.
  • proteins such as gelatin
  • polypeptides or polysaccharides such as chitosan
  • a second polyelectrolyte preferably alginate salts, cellulose derivatives guar gum, pectinate salts, carrageenan, polyacrylic and methacrylic acid or xanthan gum, or yet plant gums such as acacia gum (Gum Arabic), most preferably Gum Arabic.
  • the coacervate first material can be hardened chemically using a suitable cross-linker such as glutaraldehyde, glyoxal, formaldehyde, tannic acid or genipin or can be hardenedenzymatically using an enzyme such as transglutaminase.
  • the second polymeric material can be selected from the group consisting of polyurea, polyurethane, polyamide, polyester, polyacrylate, polysiloxane, polycarbonate, polysulfonamide, polymers of urea and formaldehyde, melamine and formaldehyde, melamine and urea, or melamine and glyoxal and mixtures thereof, preferably polyurea and/or polyurethane.
  • the second material is preferably present in an amount less than 3 wt.%, preferably less than 1 wt.% based on the total weight of the second type of microcapsule slurry.
  • the shell of the second type of microcapsules can be aminoplast-based, polyurea-based or polyurethane-based.
  • the shell of the second type of microcapsules can also be hybrid, namely organic-inorganic such as a hybrid shell composed of at least two types of inorganic particles that are cross-linked, or yet a shell resulting from the hydrolysis and condensation reaction of a polyalkoxysilane macro-monomeric composition.
  • the shell of the second type of microcapsules comprises an aminoplast copolymer, such as melamine-formaldehyde or urea- formaldehyde or cross-linked melamine formaldehyde or melamine glyoxal.
  • aminoplast copolymer such as melamine-formaldehyde or urea- formaldehyde or cross-linked melamine formaldehyde or melamine glyoxal.
  • the shell of the second type of microcapsules is polyurea- based made from, for example but not limited to isocyanate-based monomers and amine- containing crosslinkers such as guanidine carbonate and/or guanazole.
  • Certain polyurea microcapsules comprise a polyurea wall which is the reaction product of the polymerisation between at least one polyisocyanate comprising at least two isocyanate functional groups and at least one reactant selected from the group consisting of an amine (for example a water- soluble guanidine salt and guanidine); a colloidal stabilizer or emulsifier; and an encapsulated perfume.
  • an amine for example a water- soluble guanidine salt and guanidine
  • a colloidal stabilizer or emulsifier for example a colloidal stabilizer or emulsifier
  • an encapsulated perfume for example a water- soluble guanidine salt and guanidine
  • an amine for example a water-
  • the colloidal stabilizer includes an aqueous solution of between 0.1% and 0.4% of polyvinyl alcohol, between 0.6% and 1% of a cationic copolymer of vinylpyrrolidone and of a quaternized vinylimidazol (all percentages being defined by weight relative to the total weight of the colloidal stabilizer).
  • the emulsifier is an anionic or amphiphilic biopolymer, which may be, in one aspect, chosen from the group consisting of gum Arabic, soy protein, gelatin, sodium caseinate and mixtures thereof.
  • the microcapsule wall material of the second type of microcapsules may comprise any suitable resin and especially including melamine, glyoxal, polyurea, polyurethane, polyamide, polyester, etc.
  • suitable resins include the reaction product of an aldehyde and an amine
  • suitable aldehydes include, formaldehyde and glyoxal.
  • suitable amines include melamine, urea, benzoguanamine, glycoluril, and mixtures thereof.
  • Suitable melamines include, methylol melamine, methylated methylol melamine, imino melamine and mixtures thereof.
  • Suitable ureas include, dimethylol urea, methylated dimethylol urea, urearesorcinol, and mixtures thereof.
  • Suitable materials for making may be obtained from one or more of the following companies Solutia Inc. (St Louis, Missouri U.S.A.), Cytec Industries (West Paterson, New Jersey U.S.A.), Sigma-Aldrich (St. Louis, Missouri U.S.A.).
  • the second type of microcapsules is a one- shell aminoplast core-shell microcapsule obtainable by a process comprising the steps of:
  • the second type of microcapsules is a formaldehyde- free capsule.
  • a typical process for the preparation of aminoplast formaldehyde-free microcapsules slurry comprises the steps of
  • oligomeric composition comprising the reaction product of, or obtainable by reacting together: a. a polyamine component in the form of melamine or of a mixture of melamine and at least one C1-C4 compound comprising two NH2 functional groups; b. an aldehyde component in the form of a mixture of glyoxal, a C4-62,2-dialkoxy- ethanal and optionally a glyoxalate, said mixture having a molar ratio glyoxal/C4-62,2-dialkoxy-ethanal comprised between 1/1 andl0/l; and c. a protic acid catalyst;
  • an oil-in-water dispersion wherein the droplet size is comprised between 1 and 600 microns, and comprising: a. an oil; b. a water medium: c. at least an oligomeric composition as obtained in step 1 ; d. at least a cross-linker selected amongst: i. C 4 -C 12 aromatic or aliphatic di- or tri-isocyanates and their biurets, triurets, trimmers, trimethylol propane-adduct and mixtures thereof; and/or ii. a di- or tri-oxiran compounds of formula:
  • n stands for 2 or 3 and 1 represents a C2-C6 group optionally comprising from 2 to 6 nitrogen and/or oxygen atoms; e. optionally a C1-C4 compounds comprising two NH2 functional groups;
  • the second type of microcapsule comprises an oil-based core comprising a hydrophobic active, preferably perfume, optionally an inner shell made of a polymerized polyfunctional monomer; a biopolymer shell comprising a protein, wherein at least one protein is cross-linked.
  • the protein is chosen in the group consisting of milk proteins, caseinate salts such as sodium caseinate or calcium caseinate, casein, whey protein, hydrolyzed proteins, gelatins, gluten, pea protein, soy protein, silk protein and mixtures thereof, preferably sodium caseinate, most preferably sodium caseinate
  • the protein comprises sodium caseinate and a globular protein, preferably chosen in the group consisting of whey protein, beta-lactoglobulin, ovalbumine, bovine serum albumin, vegetable proteins, and mixtures thereof.
  • the protein is preferably a mixture of sodium caseinate and whey protein.
  • the biopolymer shell comprises a crosslinked protein chosen in the group consisting of sodium caseinate and/or whey protein.
  • the second type of microcapsules slurry comprises at least one microcapsule made of: an oil-based core comprising the hydrophobic active, preferably perfume; an inner shell made of a polymerized polyfunctional monomer; preferably a polyisocyanate having at least two isocyanate functional groups a biopolymer shell comprising a protein, wherein at least one protein is cross-linked; wherein the protein contains preferably a mixture comprising sodium caseinate and a globular protein, preferably whey protein, optionally at least an outer mineral layer.
  • sodium caseinate and/or whey protein is (are) crosslinked protein(s).
  • the weight ratio between sodium caseinate and whey protein is preferably comprised between 0.01 and 100, preferably between 0.1 and 10, more preferably between 0.2 and 5.
  • the second type of microcapsules is a polyamide coreshell polyamide microcapsule comprising: an oil-based core comprising comprising a hydrophobic active, preferably perfume, and a polyamide shell comprising or being obtainable from:
  • the second type of microcapsules comprises: an oil-based core comprising a hydrophobic active, preferably perfume, and a polyamide shell comprising or being obtainable from:
  • an acyl chloride preferably in an amount comprised between 5 and 98%, preferably between 20 and 98%, more preferably between 30 and 85% w/w
  • a first amino compound preferably in an amount comprised between 1 % and 50% w/w, preferably between 7 and 40% w/w;
  • a second amino compound preferably in an amount comprised between 1 % and 50% w/w, preferably between 2 and 25% w/w
  • a stabilizer preferably a biopolymer, preferably in an amount comprised between 0 and 90%, preferably between 0.1 and 75%, more preferably between 1 and 70%.
  • the second type of microcapsules comprises: an oil-based core comprising a hydrophobic active, preferably perfume, and a polyamide shell comprising or being obtainable from:
  • an acyl chloride • a first amino-compound being an amino-acid, preferably chosen in the group consisting of L-Lysine, L-Arginine, L-Histidine, L-Tryptophane and/or mixtures thereof.
  • a biopolymer chosen in the group consisting of casein, sodium caseinate, bovin serum albumin, whey protein, and/or mixtures thereof.
  • the shell of the second type of microcapsules is polyurea- or polyurethane-based.
  • processes for the preparation of polyurea and polyurethane-based microcapsule slurry are for instance described in International Patent Application Publication No. W02007/004166, European Patent Application Publication No. EP 2300146, and European Patent Application Publication No. EP25799.
  • a process for the preparation of polyurea or polyurethane-based microcapsule slurry include the following steps: a) Dissolving at least one polyisocyanate having at least two isocyanate groups in an oil to form an oil phase; b) Preparing an aqueous solution of an emulsifier or colloidal stabilizer to form a water phase; c) Adding the oil phase to the water phase to form an oil-in-water dispersion, wherein the mean droplet size is comprised between 1 and 500 pm, preferably between 5 and 50 pm; and d) Applying conditions sufficient to induce interfacial polymerisation and form microcapsules in form of a slurry.
  • microcapsules of the invention can be used in combination with active ingredients.
  • An object of the invention is therefore a composition comprising:
  • microcapsules or a microcapsule slurry as defined above (i) microcapsules or a microcapsule slurry as defined above;
  • an active ingredient preferably chosen in the group consisting of a cosmetic ingredient, skin caring ingredient, perfume ingredient, flavor ingredient, malodour counteracting ingredient, bactericide ingredient, fungicide ingredient, pharmaceutical or agrochemical ingredient, a sanitizing ingredient, an insect repellent or attractant, and mixtures thereof.
  • the capsules of the invention show a good performance in terms of stability in challenging medium.
  • Another object of the present invention is a perfuming composition
  • a perfuming composition comprising:
  • an emulsifying system i.e. a solvent and a surfactant system, or a solvent commonly used in perfumery.
  • a solvent and a surfactant system i.e. a solvent and a surfactant system
  • a detailed description of the nature and type of solvents commonly used in perfumery cannot be exhaustive.
  • solvents such as dipropyleneglycol, diethyl phthalate, isopropyl myristate, benzyl benzoate, 2-(2- ethoxy ethoxy) -1 -ethanol or ethyl citrate, which are the most commonly used.
  • compositions which comprise both a perfumery carrier and a perfumery co-ingredient can be also ethanol, water/ethanol mixtures, limonene or other terpenes, isoparaffins such as those known under the trademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company).
  • isoparaffins such as those known under the trademark Isopar® (origin: Exxon Chemical) or glycol ethers and glycol ether esters such as those known under the trademark Dowanol® (origin: Dow Chemical Company).
  • perfumery co- ingredient it is meant here a compound, which is used in a perfuming preparation or a composition to impart a hedonic effect and which is not a microcapsule as defined above.
  • perfuming co-ingredients present in the perfuming composition do not warrant a more detailed description here, which in any case would not be exhaustive, the skilled person being able to select them on the basis of his general knowledge and according to the intended use or application and the desired organoleptic effect.
  • these perfuming co-ingredients belong to chemical classes as varied as alcohols, lactones, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulfurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin.
  • co-ingredients are in any case listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of perfumery. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of perfuming compounds.
  • Co-ingredients may be chosen in the group consisting of 4-(dodecylthio)-4-(2,6,6- trimethyl-2-cyclohexen-l-yl)-2-butanone, 4-(dodecylthio)-4-(2,6,6-trimethyl-l-cyclohexen-l- yl)-2-butanone, trans-3-(dodecylthio)-l-(2,6,6-trimethyl-3-cyclohexen-l-yl)-l-butanone, 2- (dodecylthio)octan-4-one, 2-phenylethyl oxo(phenyl)acetate, 3,7-dimethylocta-2,6-dien-l-yl oxo(phenyl)acetate, (Z)-hex-3-en-l-yl oxo(phenyl)acetate, 3,7-dimethyl-2,6-octadien-l-
  • perfumery adjuvant we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, etc. A detailed description of the nature and type of adjuvant commonly used in perfuming bases cannot be exhaustive, but it has to be mentioned that said ingredients are well known to a person skilled in the art.
  • the perfuming composition according to the invention comprises between 0.01 and 30 % by weight of microcapsules as defined above.
  • microcapsules can advantageously be used in many application fields and used in consumer products.
  • Microcapsules can be used in liquid form applicable to liquid consumer products as well as in powder form, applicable to powder consumer products.
  • the consumer product as defined above is liquid and comprises: a) from 2 to 65% by weight, relative to the total weight of the consumer product, of at least one surfactant; b) water or a water-miscible hydrophilic organic solvent; and c) a microcapsule slurry or microcapsules as defined above, d) optionally non-encapsulated perfume.
  • the consumer product as defined above is in a powder form and comprises: a) from 2 to 65% by weight, relative to the total weight of the consumer product, of at least one surfactant; b) a microcapsule powder as defined above. c) optionally perfume powder that is different from the microcapsules defined above.
  • the products of the invention can in particular be of used in perfumed consumer products such as product belonging to fine fragrance or “functional” perfumery.
  • Functional perfumery includes in particular personal-care products including hair-care, body cleansing, skin care, hygiene-care as well as home-care products including laundry care, surface care and air care.
  • another object of the present invention consists of a perfumed consumer product comprising as a perfuming ingredient, the microcapsules defined above or a perfuming composition as defined above.
  • the perfume element of said consumer product can be a combination of perfume microcapsules as defined above and free or non-encapsulated perfume, as well as other types of perfume microcapsules than those here-disclosed.
  • liquid consumer product comprising: a) from 2 to 65% by weight, relative to the total weight of the consumer product, of at least one surfactant; b) water or a water-miscible hydrophilic organic solvent; and c) a perfuming composition as defined above is another object of the invention.
  • microcapsules can therefore be added as such or as part of an invention’ s perfuming composition in a perfumed consumer product.
  • perfumed consumer product it is meant a consumer product which is expected to deliver among different benefits a perfuming effect to the surface to which it is applied (e.g. skin, hair, textile, paper, or home surface) or in the air (air- freshener, deodorizer etc.).
  • a perfumed consumer product according to the invention is a manufactured product which comprises a functional formulation also referred to as “base”, together with benefit agents, among which an effective amount of microcapsules according to the invention.
  • Non- limiting examples of suitable perfumed consumer products can be a perfume, such as a fine perfume, a cologne, an after-shave lotion, a body-splash; a fabric care product, such as a liquid or solid detergent, tablets and unit dose (single or multi-chambers), a fabric softener, a dryer sheet, a fabric refresher, an ironing water, or a bleach; a personal-care product, such as a hair-care product (e.g. a shampoo, hair conditioner, a coloring preparation or a hair spray), a cosmetic preparation (e.g. a vanishing cream, body lotion or a deodorant or antiperspirant), or a skin-care product (e.g.
  • a hair-care product e.g. a shampoo, hair conditioner, a coloring preparation or a hair spray
  • a cosmetic preparation e.g. a vanishing cream, body lotion or a deodorant or antiperspirant
  • a skin-care product e.g
  • a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product a perfumed soap, shower or bath mousse, body wash, oil or gel, bath salts, or a hygiene product
  • an air care product such as an air freshener or a “ready to use” powdered air freshener
  • a home care product such all-purpose cleaners, liquid or power or tablet dishwashing products, toilet cleaners or products for cleaning various surfaces, for example sprays & wipes intended for the treatment I refreshment of textiles or hard surfaces (floors, tiles, stone-floors etc.); a hygiene product such as sanitary napkins, diapers, toilet paper.
  • Another object of the invention is a consumer product comprising: - a personal care active base, and microcapsules or a microcapsule slurry as defined above or the perfuming composition as defined above, wherein the consumer product is in the form of a personal care composition.
  • Personal care active bases in which the microcapsules of the invention can be incorporated can be found in the abundant literature relative to such products. These formulations do not warrant a detailed description here which would in any case not be exhaustive. The person skilled in the art of formulating such consumer products is perfectly able to select the suitable components on the basis of his general knowledge and of the available literature.
  • Another object of the invention is a consumer product comprising: a home care or a fabric care active base, and microcapsules or a microcapsule slurry as defined above or the perfuming composition as defined above, wherein the consumer product is in the form of a home care or a fabric care composition.
  • the consumer product comprises from 0.1 to 15 wt%, more preferably between 0.2 and 5 wt% of the microcapsules of the present invention, these percentages being defined by weight relative to the total weight of the consumer product.
  • concentrations may be adapted according to the benefit effect desired in each product.
  • An object of the invention is a consumer product, preferably a home care or a fabric care consumer product comprising the microcapsules or the microcapsule slurry as defined above, wherein the consumer product has a pH less than 7.
  • active base includes active materials (typically including surfactants) and auxiliary agents (such as bleaching agents, buffering agent; builders; soil release or soil suspension polymers; granulated enzyme particles, corrosion inhibitors, antifoaming, sud suppressing agents; dyes, fillers, and mixtures thereof).
  • active materials typically including surfactants
  • auxiliary agents such as bleaching agents, buffering agent; builders; soil release or soil suspension polymers; granulated enzyme particles, corrosion inhibitors, antifoaming, sud suppressing agents; dyes, fillers, and mixtures thereof.
  • An object of the invention is a consumer product in the form of a fabric softener composition
  • a fabric softener active base preferably comprising at least one active material chosen in the group consisting of dialkyl quaternary ammonium salts, dialkyl ester quaternary ammonium salts (esterquats), Hamburg esterquat (HEQ), TEAQ (triethanolamine quat), silicones and mixtures thereof
  • the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition, optionally free perfume oil.
  • An object of the invention is a consumer product in the form of a liquid detergent composition
  • a liquid detergent active base preferably comprising at least one active material chosen in the group consisting of anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), methyl ester sulfonate (MES) and nonionic surfactant such as alkyl amines, alkanolamide, fatty alcohol poly(ethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxy des, alkyl polyglucosides, alkyl polyglucos amides, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, a microcapsule slurry or microcapsules as defined above
  • An object of the invention is a consumer product in the form of a solid detergent composition
  • a solid detergent active base preferably comprising at least one active material chosen in the group consisting of anionic surfactant such as alkylbenzenesulfonate (ABS), secondary alkyl sulfonate (SAS), primary alcohol sulfate (PAS), lauryl ether sulfate (LES), methyl ester sulfonate (MES) and nonionic surfactant such as alkyl amines, alkanolamide, fatty alcohol poly(ethylene glycol) ether, fatty alcohol ethoxylate (FAE), ethylene oxide (EO) and propylene oxide (PO) copolymers, amine oxy des, alkyl polyglucosides, alkyl polyglucos amides, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, a microcapsule powder or microcapsule slurry or microcapsul
  • An object of the invention is a consumer product in the form of a shampoo or a shower gel composition
  • a shampoo or a shower gel active base comprising: a shampoo or a shower gel active base; preferably comprising at least one active material chosen in the group consisting of sodium alkylether sulfate, ammonium alkylether sulfates, alkylamphoacetate, cocamidopropyl betaine, cocamide MEA, alkylglucosides and aminoacid based surfactants and mixtures thereof, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition, optionally free perfume oil.
  • An object of the invention is a consumer product in the form of a rinse-off conditioner composition
  • a rinse-off conditioner active base preferably comprising at least one active material chosen in the group consisting of cetyltrimonium chloride, stearyl trimonium chloride, benzalkonium chloride, behentrimonium chloride and mixture thereof, the active base being used preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, a microcapsule slurry or microcapsules as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition, optionally free perfume oil.
  • An object of the invention is a consumer product in the form of a solid scent booster composition
  • a solid carrier preferably chosen in the group consisting of urea, sodium chloride, sodium sulphate, sodium acetate, zeolite, sodium carbonate, sodium bicarbonate, clay, talc, calcium carbonate, magnesium sulfate, gypsum, calcium sulfate, magnesium oxide, zinc oxide, titanium dioxide, calcium chloride, potassium chloride, magnesium chloride, zinc chloride, saccharides such as sucrose, mono-, di-, and polysaccharides and derivatives such as starch, cellulose, methyl cellulose, ethyl cellulose, propyl cellulose, polyols/sugar alcohols such as sorbitol, maltitol, xylitol, erythritol, and isomalt, PEG, PVP, citric acid or any water soluble solid acid, fatty alcohols or fatty acids and mixtures thereof, a microcapsule
  • An object of the invention is a consumer product in the form of a liquid scent booster composition
  • a surfactant system essentially consisting of one or more than one non-ionic surfactant, wherein the surfactant system has a mean HLB between 10 and 14, preferably chosen in the group consisting of ethoxylated aliphatic alcohols, POE/PPG (polyoxyethylene and polyoxypropylene) ethers, mono and polyglyceryl esters, sucrose ester compounds, polyoxyethylene hydroxylesters, alkyl polyglucosides, amine oxides and combinations thereof; a linker chosen in the group consisting of alcohols, salts and esters of carboxylic acids, salts and esters of hydroxyl carboxylic acids, fatty acids, fatty acid salts, glycerol fatty acids, surfactant having an HLB less than 10 and mixtures thereof, and a microcapsule slurry or microcapsules as defined above, in the form of a slurry
  • An object of the invention is a consumer product in the form of an oxidative hair coloring composition
  • an oxidizing phase comprising an oxidizing agent and an alkaline phase comprising an alkakine agent, a dye precursor and a coupling compound; wherein said dye precursor and said coupling compound form an oxidative hair dye in the presence of the oxidizing agent, preferably in an amount comprised between 85 and 99.95% by weight based on the total weight of the composition, microcapsules or a microcapsule slurry as defined above, preferably in an amount comprised between 0.05 to 15 wt%, more preferably between 0.1 and 5 wt% by weight based on the total weight of the composition, optionally free perfume oil Perfuming composition
  • the consumer product is in the form of a perfuming composition
  • a perfuming composition comprising:
  • microcapsules 0.1 to 30%, preferably 0.1 to 20% of microcapsules or a microcapsule slurry as defined previously,
  • a protein was optionally dispersed in an inert solvent (for example benzyl benzoate (BB) or Neobee) and was maintained under stirring at 60°C for 30 minutes.
  • This solution and a polyfunctional monomer for example: Benzene- 1, 3, 5-tricarbonyle chloride - BTC
  • a perfume oil 25 g or 30g - see Table 1
  • Oil phase was mixed with water (94 g), the latter comprising at least one amino compound (first amino compound) and optionally a base.
  • Reaction mixture was stirred with an Ultra Turrax at 24,000 rpm for 30 s or 1 minute to afford an emulsion.
  • At least one amino compound (second amino-compound and optionally third amino-compound) was dissolved in water (5 g) and this solution was added dropwise to the emulsion. The reaction mixture was stirred at 60°C for 4 h to afford a white dispersion.
  • second and optionally third amino-compound(s) can be added in the water phase before the emulsification step (see capsules F2-F5).
  • EDA Ethylene diamine - origin: Aldrich, Switzerland
  • DETA Diethylene triamine - origin: Aldrich, Switzerland
  • Denaturation process Solution of protein at 2% is made and NaCl is added at a concentration 100mmol/l. The solution is heated at 90°C for 90min. Once cooled down, the pH of the solution is adjusted at 9.5 with NaOH IM. This solution is then freeze dried (the solution can also be spray-dried).
  • CYS HCL Cystamine HC1, origin: Aldrich, Switzerland
  • Microcapsules of the present invention are dispersed in a fabric softener composition described in Table 8 to obtain a concentration of encapsulated perfume oil at 0.116%.
  • Table 8 Fabric conditioner composition
  • the oven program was 50°C for 5 min, 15°C/ min until 230°C and 230° C for 1 min and achieved with a 4 min post run backflush; then the column flow rate to MSD was 3.45 mL/min and -3.05mL/min to inlet with aux pressure of 30 psi.
  • the MS temperature were respectively 150°C and 230 °C for the quadrupole and the ion source, and the scan range from 25 to 450 m/z with a solvent delay of 4 min.
  • microcapsules of the present invention show good stability in challenging bases.
  • the powder was dried under vacuum (10 mBar) at 50°C until the weight of the polymer, monitored by gravimetry, was constant.
  • the resulting powder was grinded using a crusher IKA tube-mill control for Imin 30sec, suspended in Di water (0.5%w/w) and stirred at 300 RPM for 24H at RT.
  • the water was removed by filtration under vacuum over a gooch filter crucible (porosity 4) and the powder was dried at RT for 2.5 days and then under vacuum (10 mBar) at 50°C overnight.
  • the obtained powder was grinded using a crusher IKA tube-mill control for Imin and 30sec, and extracted an additional five times with ethyl acetate as described before.
  • the final powder was dried under vacuum (10 mBar) at 50°C overnight. To ensure that the totality of the perfume was removed, the sample was analyzed by GC- pyrolysis and send to biodegradation measurement following the OECD301F method.
  • the biodegradability of the exemplified analyzed shells was greater than 40% after 60 days of test.
  • Emulsions A-E having the following ingredients are prepared.
  • Table 10 Composition of Emulsions A-E and composition of granulated powder A-E after spray-drying
  • emulsion D free perfume C is added to the aqueous phase.
  • Microcapsules slurry is added to the obtained mixture. Then, the resulting mixture is then mixed gently at 25 °C (room temperature).
  • Granulated powder A-E are prepared by spray-drying Emulsion A-E using a Sodeva Spray Dryer (Origin France), with an air inlet temperature set to 215°C and a throughput set to 500 ml per hour. The air outlet temperature is of 105 °C. The emulsion before atomization is at ambient temperature.
  • Liquid scent booster composition Liquid scent booster composition
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a liquid scent booster to add the equivalent of 0.2% perfume.
  • compositions 1-6 Different ringing gel compositions are prepared (compositions 1-6) according to the following protocol.
  • aqueous phase water
  • solvent propylene glycol
  • surfactants are mixed together at room temperature under agitation with magnetic stirrer at 300 rpm for 5 min.
  • the linker is dissolved in the hydrophobic active ingredient (fragrance) at room temperature under agitation with magnetic stirrer at 300 rpm. The resulting mixture is mixed for 5 min.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a liquid detergent to add the equivalent of 0.2% perfume.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a unit dose formulation to add the equivalent of 0.2% perfume.
  • the unit dose formulation can be contained in a PVOH (polyvinyl alcohol) film.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a powder detergent composition to add the equivalent of 0.2% perfume.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a concentrated all-purpose cleaner composition to add the equivalent of 0.2% perfume.
  • Solid scent booster composition The following compositions are prepared.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a shampoo composition to add the equivalent of 0.2% perfume.
  • Nipagin Monosodium, NIPA Polyquatemium-10 is dispersed in water.
  • the remaining ingredients of phase A are mixed separately by addition of one after the other while mixing well after each adjunction. Then this pre- mix is added to the Polyquaternium-10 dispersion and was mixed for 5 min.
  • Phase B and the premixed Phase C (heat to melt Monomuls 90L-12 in Texapon NSO IS) are added. The mixture is mixed well.
  • Phase D and Phase E are added while agitating. The pH was adjusted with citric acid solution till pH: 5.5 - 6.0.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in a shampoo composition to add the equivalent of 0.2% perfume.
  • a premix comprising Guar Hydroxypropyltrimonium Chloride and Polyquatemium-10 are added to water and Tetrasodium EDTA while mixing. When the mixture is homogeneous, NaOH is added. Then, Phase C ingredients are added and the mixture was heat to 75 °C. Phase D ingredients are added and mixed till homogeneous. The heating is stopped and temperature of the mixture is decreased to RT. At 45 °C, ingredients of Phase E while mixing final viscosity is adjusted with 25% NaCl solution and pH of 5.5-6 is adjusted with 10% NaOH solution.
  • Phase A Alfa Aesar Ingredients of Phase A are mixed until an uniform mixture was obtained. Tylose is allowed to completely dissolve. Then the mixture is heated up to 70-75°C. Ingredients of Phase B are combined and melted at 70-75°C. Then ingredients of Phase B are added to Phase A with good agitation and the mixing is continued until cooled down to 60°C. Then, ingredients of Phase C are added while agitating and keeping mixing until the mixture cooled down to 40°C. The pH is adjusted with citric acid solution till pH: 3.5 - 4.0.
  • Antiperspirant spray anhydrous composition A sufficient amount of exemplified microcapsules is weighed and mixed in an antiperspirant spray anhydrous composition to add the equivalent of 0.2% perfume.
  • Aerosil® 200 trademark and origin : Evonik
  • antiperspirant spray emulsion composition A sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant spray emulsion composition to add the equivalent of 0.2% perfume.
  • Table 23 antiperspirant spray emulsion composition
  • Sensiva sc 50 trademark and origin : KRAFT
  • Aerosil R 812 ( trademark and origin : Evonik 10) Nipagin mna; trademark and origin : CLARIANT
  • Part A and Part B are weighted separately. Ingredients of Part A are heated up to 60°C and ingredients of Part B are heated to 55 °C. Ingredients of Part B are poured small parts while continuous stirring into A. Mixture were stirred well until the room temperature was reached. Then, ingredients of part C are added. The emulsion is mixed and is introduced into the aerosol cans. The propellant is crimped and added.
  • Aerosol filling 30% Emulsion: 70% Propane / Butane 2,5 bar
  • a sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant deodorant spray composition to add the equivalent of 0.2% perfume.
  • Irgasan® DP 300 trademark and origin : BASF
  • Antiperspirant roll-on emulsion composition
  • a sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant roll-on emulsion composition to add the equivalent of 0.2% perfume.
  • Part A and B are heated separately to 75 °C; Part A is added to part B under stirring and the mixture is homogenized for 10 minutes. Then, the mixture is cooled down under stirring; and part C is slowly added when the mixture reached 45 °C and part D when the mixture reached at 35 °C while stirring. Then the mixture is cooled down to RT.
  • antiperspirant roll-on composition A sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant roll-on composition to add the equivalent of 0.2% perfume. Table 26: antiperspirant roll-on composition
  • part B The ingredients of part B are mixed in the vessel then ingredient of part A is added. Then dissolved part C in part A and B. With perfume, 1 part of Cremophor RH40 for 1 part of perfume is added while mixing well
  • a sufficient amount of exemplified microcapsules is weighed and mixed in antiperspirant roll-on emulsion composition to add the equivalent of 0.2% perfume.
  • Part A is prepared by sprinkling little by little the Hydroxyethylcellulose in the water whilst rapidly stirring with the turbine. Stirring is continued until the Hydroxy ethylcellulose is entirely swollen and giving a limpid gel. Then, Part B is poured little by little in Part A whilst continuing stirring until the whole is homogeneous. Part C is added.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • Cremophor® RH 40 trademark and origin : BASF
  • Ingredients from Part B are mixed together. Ingredients of Part A are dissolved according to the sequence of the Table and are poured into part B.
  • a sufficient amount of granules A-E is weighed and mixed in introduced in a standard talc base: 100% talc, very slight characteristic odor, white powder, origin: LUZENAC to add the equivalent of 0.2% perfume.
  • KATHON CG trademark and origin: ROHM & HASS Ingredients are mixed, pH is adjusted to 6-6.3 (Viscosity: 4500cPo +/-1500cPo (Brookfield RV / Spindle#4 / 20RPM)).
  • a sufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • a sufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • EUPERLAN PK 3000 AM trademark and origin: COGNIS
  • a sufficient amount of exemplified microcapsules is weighed and mixed in the following composition to add the equivalent of 0.2% perfume.
  • a sufficient amount of a microcapsule slurry M (prepared according to the protocol disclosed in example 1 except that a menthol flavor is encapsulated) is weighed and mixed in the following composition to add the equivalent of 0.2% flavor.
  • a sufficient amount of a microcapsule slurry M (prepared according to the protocol disclosed in example 1 except that a menthol flavor is encapsulated) is weighed and mixed in the following composition to add the equivalent of 0.2% flavor.
  • Aerosil®200 trademark and origin:
  • a sufficient amount of a microcapsule slurry M (prepared according to the protocol disclosed in example 1 except that a menthol flavor is encapsulated) is weighed and mixed in the following composition to add the equivalent of 0.2% flavor.
  • a sufficient amount of a microcapsule slurry M (prepared according to the protocol disclosed in example 1 except that a menthol flavor is encapsulated) is weighed and mixed in the following composition to add the equivalent of 0.2% flavor.
  • Table 37 Mouthwash formulation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne un nouveau procédé de préparation de microcapsules à base de protéines végétales. L'invention concerne également des microcapsules à base de protéines végétales. L'invention concerne par ailleurs des compositions parfumantes et des produits de consommation comprenant lesdites microcapsules, en particulier des produits de consommation parfumés se présentant sous la forme de produits de soins de santé ou de soins personnels.
EP22797327.8A 2021-10-04 2022-09-27 Microcapsules à base de protéines végétales Pending EP4376996A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP21200666 2021-10-04
EP21205885 2021-11-02
PCT/EP2022/076819 WO2023057262A1 (fr) 2021-10-04 2022-09-27 Microcapsules à base de protéines végétales

Publications (1)

Publication Number Publication Date
EP4376996A1 true EP4376996A1 (fr) 2024-06-05

Family

ID=84044106

Family Applications (1)

Application Number Title Priority Date Filing Date
EP22797327.8A Pending EP4376996A1 (fr) 2021-10-04 2022-09-27 Microcapsules à base de protéines végétales

Country Status (3)

Country Link
EP (1) EP4376996A1 (fr)
MX (1) MX2024002117A (fr)
WO (1) WO2023057262A1 (fr)

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1142500A (fr) 1979-03-28 1983-03-08 Grace (W.R.) & Co. Procede cyclique pour l'obtention de catalyseur zsm-5 de haute purete
WO2007004166A1 (fr) 2005-06-30 2007-01-11 Firmenich Sa Microcapsules de polyurethane et de polyuree
US8426353B2 (en) 2008-06-16 2013-04-23 Firmenich Sa Process for preparing polyurea microcapsules
GB201011905D0 (en) 2010-07-15 2010-09-01 Unilever Plc Benefit delivery particle,process for preparing said particle,compositions comprising said particles and a method for treating substrates
ES2569045T3 (es) 2011-08-24 2016-05-06 Unilever N.V. Partículas de suministro de un agente de beneficio que comprenden polisacáridos no iónicos
MX2019006202A (es) 2016-12-22 2019-08-21 Firmenich & Cie Microcapsulas de perfume de alto impacto de densidad balanceada.
EP3746217A1 (fr) * 2018-06-21 2020-12-09 Firmenich SA Procédé de préparation de microcapsules
BR112021011819A2 (pt) * 2018-12-18 2021-08-31 International Flavors & Fragrances Inc. Composição de microcápsula, processo para preparar uma composição de microcápsula, e, produto de consumo
BR112021011885A2 (pt) * 2018-12-18 2021-08-31 International Flavors & Fragrances Inc. Composição de microcápsula, produto de consumo, e, método para preparar uma composição de microcápsula
US20220226797A1 (en) * 2019-04-12 2022-07-21 International Flavors & Fragrances Inc. Sustainable core-shell microcapsules prepared with combinations of cross-linkers
EP3952823A4 (fr) * 2019-04-12 2023-08-30 International Flavors & Fragrances Inc. Produit de consommation avec des compositions de microcapsules à coeur-enveloppe biodégradables à libération contrôlée
DE202020005910U1 (de) * 2019-12-19 2023-03-16 Firmenich Sa Parfümformulierung für Abgabesystem
WO2021122633A1 (fr) * 2019-12-19 2021-06-24 Firmenich Sa Système de distribution de parfum
US20230134756A1 (en) 2020-03-16 2023-05-04 Firmenich Sa Microcapsules coated with a polysuccinimide derivative
MX2022011099A (es) * 2020-03-27 2022-10-03 Firmenich & Cie Microcapsulas coacervadas de nucleo-cubierta.

Also Published As

Publication number Publication date
WO2023057262A1 (fr) 2023-04-13
MX2024002117A (es) 2024-03-06

Similar Documents

Publication Publication Date Title
JP7523443B2 (ja) ポリアミドマイクロカプセルの製造方法
WO2020127743A1 (fr) Microcapsules de polyamide
EP3894063A1 (fr) Microcapsules de poly(ester-urée)
WO2024018014A1 (fr) Microcapsules composites
EP4308287A1 (fr) Microcapsules à base de polyamide
US20240050331A1 (en) Process for preparing microcapsules
US20240156710A1 (en) Functionalized chitosan preparation
US20240148617A1 (en) Coated core-shell microcapsules
US20240076583A1 (en) Hybrid microcapsules comprising a regenerated biopolymer
US20230105666A1 (en) Polyamide microcapsules
EP4376996A1 (fr) Microcapsules à base de protéines végétales
WO2024126450A1 (fr) Microcapsules à base de protéines
WO2024126446A1 (fr) Microcapsules à base de polyamide
WO2023006532A1 (fr) Microcapsules à base de polyamide
US20240252404A1 (en) Polyamide-based microcapsules
WO2023217589A1 (fr) Microcapsules de polyamide
WO2023217590A1 (fr) Microcapsules de polyamide
WO2024008583A1 (fr) Microcapsules hybrides
WO2024153727A1 (fr) Microcapsules obtenues à partir d'un prépolymère à base de polylactone
CN117897223A (zh) 植物蛋白基微胶囊
CN117460573A (zh) 聚酰胺基微胶囊
CN117813154A (zh) 聚酰胺基微胶囊

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20240301

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR